1,8-Diaminonaphthalene → 4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride

HRID 419720

반응식

HRID 419720 반응식
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH3:28])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C1(N)C2C(=CC=CC=2N)C=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[ClH:26].[Cl:26][C:21]1[CH:20]=[C:19]([C:17]2[N:18]=[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]([CH2:27][CH3:28])[CH:16]=2)[CH:24]=[CH:23][C:22]=1[F:25]

참가 물질

5

반응물 3

HCID 680671,8-DiaminonaphthaleneHCID 5213051-Chloroethyl chloroformateHCID 666498541-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine

생성물 1

HCID 666499424-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride수율 235.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Dissolve 1-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine (263.3 mg, 1.00 equiv; 0.662 mmoles) and 1,8-Naphthalenediamine, N,N,N′,N′-Tetramethyl-(0.05 equiv, 0.033 mmoles, 7.0 mg) in 1,2-Dichloro-ethane (5 mL) and cool in an ice bath. Add 1-chloroethyl chloroformate (1.2 equiv, 0.794 mmol; 0.086 mL). Stir the reaction 10 minutes in an ice bath then heat to reflux for 20 minutes and evaporate to dryness. Dissolve the residue in methanol (5 mL) and reflux for 45 minutes and evaporate to dryness to give 268 mg (0.779 mmol, 118%) 4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride.

후처리

  1. temperaturecool in an ice bath
  2. customthe reaction 10 minutes in an ice bath
  3. temperaturethen heat
  4. temperatureto reflux for 20 minutes
  5. customevaporate to dryness
  6. dissolutionDissolve the residue in methanol (5 mL)
  7. temperaturereflux for 45 minutes
  8. customevaporate to dryness

출처 및 근거

ORD 기록
ord-f58beba155f34212b5c2341dbd4e0be3
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093383B2

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