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

HRID 20305

反応式

HRID 20305 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 (5.11 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-48e4777ee5c849119137dbc7f8327e03
出典データセット
uspto-grants-2010_06
特許番号
US07745638B2

関連ノート

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