Water → N-alpha-phenyl-ethyl-3,4-dimethoxy-amphetamine

HRID 1376870노트

반응식

HRID 1376870 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:6][C@H:7]([CH3:9])[NH2:8].CO[C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1OC)[CH2:20][C@@H:21](C)N.O>C1C=CC=CC=1>[C:19]1([CH:20]([NH:8][CH:7]([CH2:6][C:5]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:9])[CH3:21])[CH:24]=[CH:25][CH:26]=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11095534(2S)-1-(3,4-Dimethoxyphenyl)propan-2-amineHCID 117694083,4-Dma, (R)-

생성물 1

HCID 22918570N-alpha-phenyl-ethyl-3,4-dimethoxy-amphetamine

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Said synthesis was developed by D. E. Nichols et al. ("J. Med. Chem.", 1973, 16, 480-48 and U.S. Pat. No. 4,000,197, of 12.28.1976) and was applied to the chiral synthesis of several methoxylated amphetamines, including (S)-3,4-dimethoxy-amphetamine, which is an enantiomer of (3). In U.S. Pat. No. 4,000,197, the synthesis of the iminic intermediate is carried out in benzene under refluxing conditions during 24 hours with formed water being simultaneously azeotroped off; the hydrogenation is carried out with Raney-Nickel as the catalyst, in absolute ethanol under medium-pressure hydrogen (3 atm of H2). The N-α-phenyl-ethyl-3,4-dimethoxy-amphetamine (15) intermediate is isolated as hydrochloride salt, by crystallization in aqueous acetone or acetone/isopropanol blend, in moderate yield (relatively to dimethoxy-phenyl-acetone), of 48%.

후처리

  1. customSaid synthesis
  2. custom4,000,197, the synthesis of the iminic intermediate
  3. customsimultaneously azeotroped off

출처 및 근거

ORD 기록
ord-c4c02e9e2f2443b689ae59a997b92cbf
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663360

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