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

HRID 394117

反応式

HRID 394117 の反応式
ClCCl.[C:4]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([CH3:7])([CH3:6])[CH3:5].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:15]([NH:22][CH:11]1[CH2:12][CH2:13][N:8]([C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:9][CH2:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 7504BenzylamineHCID 738401-tert-Butyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A dichloromethane solution (3 mL) containing 1-tert-butylpiperidin-4-one (COMPOUND PPA-1) (120 mg, 0.77 mmol), benzyl amine (0.17 mL, 1.56 mmol), acetic acid (0.05 mL) and sodium triacetoxy borohydride (246 mg, 1.16 mmol) was stirred for several days. The solution was concentrated and the residue partitioned between aqueous potassium carbonate and ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography using CHCl3/MeOH/NH4OH (87/12/1) as eluent to give N-benzyl-1-tert-butylpiperidin-4-amine. Mass spectrum (ESI) 247 (M+1). 1H NMR (500 MHz, CD3OD): δ 1.09(s, 9H); 1.38-1.48(m, 2H); 1.91-1.97(m, 2H); 2.11-2.18(m, 2H); 2.40-2.48(m, 1H); 3.02-3.08(m, 2H); 3.76(s, 2H); 4.87(s, 1H); 7.21-7.26(m, 1H); 7.29-7.36(m, 4H).

後処理

  1. concentrationThe solution was concentrated
  2. customthe residue partitioned between aqueous potassium carbonate and ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-951f91de6844404bb8d38cbe2efb772d
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

関連ノート

読み込み中…