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

HRID 394117

반응식

HRID 394117 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-951f91de6844404bb8d38cbe2efb772d
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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