Nefazodone → Nefazodone Hydrochloride

HRID 1153958

反応式

HRID 1153958 の反応式
[Na].O(CCBr)C1C=CC=CC=1.[Cl:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][N:28]3[C:32](=[O:33])[N:31]([CH2:34][CH2:35][O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:30]([CH2:43][CH3:44])=[N:29]3)[CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1>C1(C)C(C)=CC=CC=1>[ClH:12].[Cl:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][CH2:27][N:28]3[C:32](=[O:33])[N:31]([CH2:34][CH2:35][O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:30]([CH2:43][CH3:44])=[N:29]3)[CH2:23][CH2:24]2)[CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 4449NefazodoneHCID 68526Benzene, (2-bromoethoxy)-HCID 5360545Sodium

生成物 1

HCID 54911Nefazodone Hydrochloride収率 30.7%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒2 回

実験手順

The sodium salt is pulverized, suspended in 200 ml. of xylene and mixed with phenoxyethyl bromide (10.4 g., 0.052 mole) in 20 ml. of xylene. The resulting mixture is refluxed with stirring for a 64 hr. period and the hot reaction mixture filtered. The filtrate is concentrated under reduced pressure and residual material taken up in ether. Insolubles are collected and the ether filtrate concentrated to afford 22.9 g. (94%) of 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one as the free base. Purification of the product is carried out by acidifying a solution of the free base in ethanol with ethanolic hydrogen chloride, and crystallization to afford hydrated (0.25 mole) 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one hydrochloride, m.p. 175°-177° C. (30.7% yield).

後処理

  1. temperatureThe resulting mixture is refluxed
  2. filtrationperiod and the hot reaction mixture filtered
  3. concentrationThe filtrate is concentrated under reduced pressure and residual material
  4. customInsolubles are collected
  5. concentrationthe ether filtrate concentrated
  6. customto afford 22.9 g
  7. customPurification of the product
  8. customwith ethanolic hydrogen chloride, and crystallization

出典と根拠

ORDレコード
ord-0ab313554d974c51af90e245d6559d77
出典データセット
uspto-grants-1984_12
特許番号
US04487773

関連ノート

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