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

HRID 1354097ノート

反応式

HRID 1354097 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-934a0acd65c441f4b2ef6d8b3264d1ea
出典データセット
uspto-grants-2007_05
特許番号
US07223767B2

反応ノート

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