1-(2-Chloroethyl)pyrrolidine → 4-Adamantoyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline Dihydrochloride Dihydrate

HRID 2050209

反応式

HRID 2050209 の反応式
CNC1C=CC([O:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)=CC=1.[Li]CCCC.[Cl:25]CCN1CCCC1.[OH2:33].O.[ClH:35].Cl.[C:37]12([O:47][C:48]3[CH:62]=[CH:61][C:51]([N:52]([CH3:60])[CH2:53][CH2:54][N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)=[CH:50][CH:49]=3)CC3CC(CC(C3)C1)C2>CCCCC.C1C=CC=CC=1.C1COCC1.C1(C)C=CC=CC=1.CO>[OH2:9].[OH2:47].[ClH:25].[ClH:35].[C:10]12([C:37]([O:47][C:48]3[CH:62]=[CH:61][C:51]([N:52]([CH3:60])[CH2:53][CH2:54][N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)=[CH:50][CH:49]=3)=[O:33])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2

参加物

10

反応物 4

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 12510299N-Methyl-p-(1-adamantyloxy)anilineHCID 203421994-adamantyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline dihydrochloride dihydrateHCID 178418339Butyllithium

生成物 1

HCID 705880674-Adamantoyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline Dihydrochloride Dihydrate

試薬・触媒・溶媒 5

HCID 241Benzene溶媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice:MeOH cooled solution of 2.0 g. (0.0078 mole) of N-Methyl-p-(1-adamantyloxy)aniline in 20 ml. THF was added 4.75 ml. of 1.64 N BuLi in pentane. A solution of a 1:1 mixture of toluene, and 1-chloro-2-pyrrolidino ethane (2.08 g.) in 20 ml. THF was then added and the mixture stirred at room temperature for 1 hour and at reflux for 18 hours. The solution was allowed to cool, diluted with C6H6 and washed with H2O and brine. The residue remaining when the organic fraction was taken to dryness was dissolved in CH2Cl2, treated with 10 ml. HCl saturated Et2O and taken to dryness. The residual solid was recrystallized from CH2Cl2 :CH3CN to yield 1.93 g. (55%) of 4-adamantyloxy-N-methyl-N-(2-pyrrolidinoethyl)aniline dihydrochloride dihydrate, m.p. 189°-190° (efervess).

後処理

  1. temperatureat reflux for 18 hours
  2. temperatureto cool
  3. washwashed with H2O and brine
  4. dissolutionwas dissolved in CH2Cl2
  5. additiontreated with 10 ml
  6. customThe residual solid was recrystallized from CH2Cl2
  7. customCH3CN to yield 1.93 g

出典と根拠

ORDレコード
ord-fcb9e0995f07481c99b0d716c6297a28
出典データセット
uspto-grants-1980_04
特許番号
US04200588

関連ノート

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