Trifluoroacetic acid → 2-(1-piperidin-4-yl-ethyl)-3H-quinazolin-4-one

HRID 238238Notes

Reaction equation

HRID 238238 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[NH:25][C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[NH:25][C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH3:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1361115114-[1-(4-Oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1361115042-(1-piperidin-4-yl-ethyl)-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[1-(4-oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester and TFA in CH2Cl2 was stirred at r.t. for 6 hr. The precipitated solid was filtered and dried to afford the product as a white solid. (2 g, 90%). 1H NMR (DMSO-d6) δ 8.51 (br, s, 1H), 8.18 (br, s, 1H), 8.06 (d, 1H, J=7.6), 7.74 (t, 1H, J=8.0), 7.57 (d, 1H, J=8.0), 7.44 (t, 1H, J=8.0), 3.29-3.18 (m, 2H), 2.88-2.76 (m, 2H), 2.61-2.57 (m, 1H), 1.95-1.92 (m, 2H), 1.61-1.57 (m, 1H), 1.42-1.25 (m, 2H), 1.25 (d, 3H, J=6.8); ESI-MS m/z 258.1 (M+1)+.

Workup

  1. filtrationThe precipitated solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-2c0792c56e7c4ce9a8d3da1452c94d7b
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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