Triethylamine → 3-Phenyl[(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methyl]benzene

HRID 651722

반응식

HRID 651722 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[C:16]1([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:9]1([C:5]2[CH:4]=[C:3]([CH2:2][N:25]3[CH2:24][CH:23]=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:27][CH2:26]3)[CH:8]=[CH:7][CH:6]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27238604-Phenyl-1,2,3,6-tetrahydropyridine hydrochlorideHCID 154808923-(Chloromethyl)-1,1'-biphenyl

생성물 1

HCID 155212333-Phenyl[(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methyl]benzene

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 45 mg of 3-chloromethylbiphenyl in 5 mL of chloroform was added 50 mg of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride and 0.5 mL triethylamine. The reaction mixture was heated at reflux temperature overnight, cooled to room temperature, washed successively with 50 mL aliquots of dilute sodim hydroxide and brine. The chloroform was removed by evaporation under reduced pressure to yield 3-phenyl[(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methyl]benzene which was purified by chromatography on silica gel using 5% methanol in dichloromethane as eluent. Evaporation of the solvent yielded a solid which was treated with ethereal-HCl to give 15 mg of 3-[(4-1,2,3,6-tetrahydropyridin-1-yl)methyl]biphenyl hydrochloride (Compound 3), mp 236-238° C.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature overnight
  3. washwashed successively with 50 mL aliquots of dilute sodim hydroxide and brine
  4. customThe chloroform was removed by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-d63c70e1a41547b2ae4a67444001d7e2
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281359B1

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