Methanol → 4-(1-Adamantyloxy)-N-methyl-N-[3-(dimethylamino)propyl]aniline

HRID 2050210ノート

反応式

HRID 2050210 の反応式
CO.[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)=[CH:7][CH:6]=1.[Li][CH2:23]CCC.Cl[CH:28]([N:31]([CH3:33])[CH3:32])[CH2:29]C>CCCCC.C1COCC1.C1(C)C=CC=CC=1>[C:12]12([O:11][C:8]3[CH:7]=[CH:6][C:5]([N:4]([CH3:23])[CH2:3][CH2:29][CH2:28][N:31]([CH3:33])[CH3:32])=[CH:10][CH:9]=3)[CH2:21][CH:16]3[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]3)[CH2:19]1)[CH2:13]2

参加物

8

反応物 4

HCID 887MethanolHCID 12510299N-Methyl-p-(1-adamantyloxy)anilineHCID 22278018(1-Chloropropyl)dimethylamineHCID 178418339Butyllithium

生成物 1

HCID 125103294-(1-Adamantyloxy)-N-methyl-N-[3-(dimethylamino)propyl]aniline

試薬・触媒・溶媒 3

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. (0.078 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-N,N-dimethyl propyl amine in 20 ml. THF was then added and the mixture stirred at room temperature for 1 hour and at reflux for 20 hours. The bulk of the solvent was removed in vacuum and the residue dissolved in H2O and Et2O. The organic layer was washed with H2O and brine and taken to dryness. The residue was dissolved in CH2Cl2, treated with an excess of HCl in Et2O and taken to dryness. The remaining solid was recrystallized from MeOH:CH3CN to give 1.72 g. (53%) of 4'-(1-adamantyloxy)-N-methyl-N-[3-(dimethylamino)propyl]aniline, m.p. 221°-223°.

後処理

  1. temperatureat reflux for 20 hours
  2. customThe bulk of the solvent was removed in vacuum
  3. dissolutionthe residue dissolved in H2O
  4. washThe organic layer was washed with H2O and brine
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. additiontreated with an excess of HCl in Et2O
  7. customThe remaining solid was recrystallized from MeOH
  8. customCH3CN to give 1.72 g

出典と根拠

ORDレコード
ord-f52bc419c27943649cc63233a51eb0c4
出典データセット
uspto-grants-1980_04
特許番号
US04200588

反応ノート

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