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Hydrochloric Acid → 5,5-Dimethyl-10-[2-methyl-4-(piperidino)butyryloxy]-8-(4-fluorophenyl-1-methylbutyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine hydrochloride

HRID 2398867
ノート
印刷プレビュー

反応式

HRID 2398867 の反応式
[CH3:1][C:2]1([CH3:32])[C:24]2[CH2:25][CH2:26][N:27]([CH2:29][C:30]#[CH:31])[CH2:28][C:23]=2[C:5]2[C:6]([OH:22])=[CH:7][C:8]([C:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)([CH3:14])[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3]1.[ClH:33].[CH3:34][CH:35]([CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:36](O)=[O:37].C1(N=C=NC2CCCCC2)CCCCC1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.Cl>C(Cl)Cl.C1CCCCC1.C(Cl)Cl.C(OCC)C.C(OCC)C.C(Cl)Cl>[ClH:33].[CH3:32][C:2]1([CH3:1])[C:24]2[CH2:25][CH2:26][N:27]([CH2:29][C:30]#[CH:31])[CH2:28][C:23]=2[C:5]2[C:6]([O:22][C:36](=[O:37])[CH:35]([CH3:34])[CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)=[CH:7][C:8]([C:10]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)([CH3:14])[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 211526892-Methyl-4-piperidin-1-yl-butyric acid hydrochlorideHCID 538194395,5dimethyl-10-hydroxy-8-(4-fluorophenyl-1-methylbutyl)-2(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine

生成物 1

HCID 88808909
5,5-Dimethyl-10-[2-methyl-4-(piperidino)butyryloxy]-8-(4-fluorophenyl-1-methylbutyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine hydrochloride

試薬・触媒・溶媒 4

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 21881112Ethyl ether methylene chloride溶媒HCID 21916607Dichloromethane cyclohexane溶媒

実験手順

2.0 g. (5.05 mm.) of 5,5-dimethyl-10-hydroxy-8-(4-fluorophenyl-1-methylbutyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine are combined with 1.12 g. (5.05 mm.) of α-methyl-γ-piperidino butyric acid hydrochloride and 1.08 g. (5.25 mm.) of dicyclohexylcarbodiimide in 110 ml. of methylene chloride and the mixture is stirred at room temperature for 16 hours. After cooling for 4 hours, the by-product of dicyclohexylurea is removed by suction filtration. The mother liquor is evaporated to give a colorless foamy residue which is dissolved in a methylene chloride/cyclohexane mixture and stored for 16 hours in the cold. A small amount of solid is separated by gravity filtration, and the solvents are removed using a rotary evaporator. The residue is dried to give a colorless solid which is dissolved in a mixture of methylene chloride/diethyl ether and converted to the dihydrochloride by the addition of a solution of hydrogen chloride is diethyl ether. The solvents are decanted, and the gummy residue crystallized upon trituration with diethyl ether. The solid is filtered and recrystallized from 20 ml. of methylene chloride/20 ml. diethyl ether to give the desired product.

後処理

  1. temperatureAfter cooling for 4 hours
  2. customthe by-product of dicyclohexylurea is removed by suction filtration
  3. customThe mother liquor is evaporated
  4. customto give a colorless foamy residue which
  5. customA small amount of solid is separated by gravity filtration
  6. customthe solvents are removed
  7. customa rotary evaporator
  8. customThe residue is dried
  9. customto give a colorless solid which
  10. customThe solvents are decanted
  11. customthe gummy residue crystallized upon trituration with diethyl ether
  12. filtrationThe solid is filtered
  13. customrecrystallized from 20 ml

出典と根拠

ORDレコード
ord-0281ea2529af433292dff27f5945434d
出典データセット
uspto-grants-1977_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04025630

反応ノート

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