Nefazodone → Nefazodone Hydrochloride

HRID 1153958

반응식

HRID 1153958 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 54911Nefazodone Hydrochloride수율 30.7%

시약·촉매·용매 1

HCID 7237O-Xylene용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0ab313554d974c51af90e245d6559d77
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04487773

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