Dimethylformamide → 3,4-dihydro-7-methoxy-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone

HRID 2217274Notes

Reaction equation

HRID 2217274 reaction equation
[NH2:1][C:2]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.CN(C)[CH:27]=[O:28].[K+].[Br-]>C(OC)(C)(C)C>[CH3:24][O:23][C:21]1[CH:22]=[C:2]2[C:3]([CH2:4][N:5]([CH:6]3[CH2:11][CH2:10][N:9]([CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:8][CH2:7]3)[C:27](=[O:28])[NH:1]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 253877Potassium BromideHCID 179586822-amino-4-methoxy-N-(1-phenylmethyl-4-piperidinyl)-benzylamine

Product 1

HCID 179586843,4-dihydro-7-methoxy-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.5 g (7.682 mmol) of 2-amino-4-methoxy-N-(1-phenylmethyl-4-piperidinyl)-benzylamine, 1.62 g (10 mmol) of N,N′-carbonyldiimidazole, and 25 mL of dimethylformamide was heated to 90° C. with stirring for 2.5 hours. After cooling, the mixture was stirred into 100 mL of ice water, the suspension formed was overlaid with 10 mL of tert-butylmethylether, the precipitate formed was suction filtered, washed with water, and then with tert-butylmethylether. After drying in vacuo, 1.9 g (70% of theoretical) of colorless crystals were obtained. IR (KBr): 1664 (C═O) cm−1; MS: M+=351.

Workup

  1. temperatureAfter cooling
  2. customthe suspension formed
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. customAfter drying in vacuo, 1.9 g (70% of theoretical) of colorless crystals
  7. customwere obtained

Sources & evidence

ORD record
ord-2e13f2dfea614e599e2939fa386e69de
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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