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

HRID 419720

反応式

HRID 419720 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f58beba155f34212b5c2341dbd4e0be3
出典データセット
uspto-grants-2012_01
特許番号
US08093383B2

関連ノート

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