Benzylamine → 1-(1,1-dimethylethyl)-N-(phenylmethyl)-4-Piperidinamine

HRID 659788

反応式

HRID 659788 の反応式
[C:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:12]([NH:19][CH:8]1[CH2:9][CH2:10][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 7504BenzylamineHCID 738401-tert-Butyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 226479391-(1,1-dimethylethyl)-N-(phenylmethyl)-4-Piperidinamine収率 26.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 1-tert-butyl-4-oxopiperidine (3.6 g, 23.1), benzylamine (5.1 ml, 46.8 mmol), acetic acid (1.5 ml) and sodium triacetoxyborohydride (7.38 g, 34.8 mmol) was stirred at ambient for 2 days. Reaction mixture reduced in vacuo, residue partitioned between aqueous K2CO3 and EtOAc. The organic portion was dried (Na2SO4), filtered and reduced in vacuo. The residue was subjected to chromatography using CH2Cl2/MeOH/NH4OH (87/12/1) as the eluent to yield N-benzyl-1-tert-butylpiperidin-4-amine (1.5 g) (LC/MS: Rt 0.45, [M+H]+ 247).

後処理

  1. customReaction mixture
  2. custompartitioned between aqueous K2CO3 and EtOAc
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-49a1ebe5ca1e4759981e9da023f1486c
出典データセット
uspto-grants-2011_12
特許番号
US08080666B2

関連ノート

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