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

HRID 1354097Notes

Reaction equation

HRID 1354097 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-934a0acd65c441f4b2ef6d8b3264d1ea
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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