Ammonium Hydroxide → Cyclopropylmethyl-(2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydro-quinazolin-4-yl)-propyl-amine

HRID 1354097노트

반응식

HRID 1354097 반응식
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:18])([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:5]=[C:4]([CH3:19])[N:3]=1.[CH2:20]([NH:23][CH2:24][CH:25]1[CH2:27][CH2:26]1)[CH2:21][CH3:22].[NH4+].[OH-]>CN1CCCC1=O>[CH:25]1([CH2:24][N:23]([C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][C:7]([CH3:18])([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:6]=3[N:5]=[C:4]([CH3:19])[N:3]=2)[CH2:20][CH2:21][CH3:22])[CH2:27][CH2:26]1

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 117787Cyclopropanemethanamine, N-propyl-HCID 211043804-Chloro-2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydroquinazoline

생성물 1

HCID 11348656Cyclopropylmethyl-(2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydro-quinazolin-4-yl)-propyl-amine수율 36.8%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A solution of 4-chloro-2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydroquinazoline (180 mg, 0.7 mmol), N-propylcyclopropanemethylamine (1 mL, 7 mmol) and 1 mL of 1-methyl-2-pyrrolidinone was heated in an oil bath at 160-170° C. for 3 h. After cooling, the mixture was added to aqueous NH4OH and extracted with ethyl acetate. The extract was washed with 1N NaOH and brine, dried, (sodium sulfate) and evaporated. Purification by flash chromatography (15% ethyl acetate/hexane) afforded 90 mg of cyclopropylmethyl-(2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydro-quinazolin-4-yl)-propyl-amine as an oil. MS MH+ 349.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N NaOH and brine
  4. customdried
  5. custom(sodium sulfate) and evaporated
  6. customPurification by flash chromatography (15% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-934a0acd65c441f4b2ef6d8b3264d1ea
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223767B2

반응 노트

불러오는 중…