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

HRID 1376870ノート

反応式

HRID 1376870 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-c4c02e9e2f2443b689ae59a997b92cbf
出典データセット
uspto-grants-1997_09
特許番号
US05663360

反応ノート

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