tert-Butyl 2-((1-benzylpiperidin-4-ylamino)methyl)-6-fluorophenylcarbamate → 3-(1-Benzylpiperidin-4-yl)-8-fluoro-3,4-dihydroquinazolin-2(1H)-one

HRID 501974Notes

Reaction equation

HRID 501974 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=2[NH:23][C:24](=[O:30])OC(C)(C)C)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:15][C:16]3[C:17](=[C:18]([F:22])[CH:19]=[CH:20][CH:21]=3)[NH:23][C:24]2=[O:30])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59424374tert-Butyl 2-((1-benzylpiperidin-4-ylamino)methyl)-6-fluorophenylcarbamate

Product 1

HCID 211021543-(1-Benzylpiperidin-4-yl)-8-fluoro-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl 2-((1-benzylpiperidin-4-ylamino)methyl)-6-fluorophenylcarbamate (83.0 g, 201 mmol) was dissolved in pyridine (600 mL) and heated at reflux for 12 h. The reaction was concentrated, triturated with hot diethyl ether and placed in the freezer overnight. The resulting solid was filtered to give 68.1 g (64%) as a white solid. 1H-NMR (CDCl3, 500 MHz) δ 1.68 (m, 2H), 1.86 (dddd, J=11.9, 11.9, 11.9, 3.4 Hz, 2H), 2.14 (dd, J=11.6, 10.1 Hz, 2H), 2.98 (d, J=11.6 Hz, 2H), 3.51 (s, 2H), 4.34-4.44 (m, 3H), 6.71 (bs, 1H), 6.79-6.89 (m, 2H), 6.94 (dd, J=9.2, 9.2 Hz, 1H), 7.21-7.34 (m, 5H). Mass spec.: 340.30 (MH)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 h
  3. concentrationThe reaction was concentrated
  4. customtriturated with hot diethyl ether
  5. customplaced in the freezer overnight
  6. filtrationThe resulting solid was filtered
  7. customto give 68.1 g (64%) as a white solid

Sources & evidence

ORD record
ord-5e586d3c0a7145588a386669250b58f6
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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