Trifluoroacetic acid → 7-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one

HRID 1520118Notes

Reaction equation

HRID 1520118 reaction equation
[O:1]=[C:2]1[NH:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)=[CH:7][CH:8]=2)[NH:3]1.FC(F)(F)C(O)=O>>[NH:15]1[CH2:14][CH2:13][CH:12]([C:6]2[CH:5]=[C:4]3[C:9]([CH2:10][NH:11][C:2](=[O:1])[NH:3]3)=[CH:8][CH:7]=2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117796385tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)piperidine-1-carboxylate

Product 1

HCID 1177595727-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneYield 95%

Procedure

Following the same procedure adopted for the synthesis of 5, treatment of compound 23 with trifluoroacetic acid afforded the title compound 6 as a dark brown gum (95%). IR (KBr) νmax. cm−1: 3271 (NH), 3032 (Ar—H), 1688 (C═O), 1610, 1515, 1412 (C═C). 1H NMR (500 MHz, CDCl3) δ=1.71 (m, 2H, CH2); 1.85 (m, 2H, CH2); 2.75 (m, 1H, CH); 2.95 (m, 2H, CH2); 3.32 (m, 2H, CH2); 5.23 (s, 2H, CH2); 6.82 (d, 1H, J=8.2 Hz, aromatic H); 7.02 (s, 1H, aromatic H); 7.09 (d, 1H, J=8.1 Hz, aromatic H); 8.61 (br. s, 1H, NH); 8.87 (br. s, 1H, NH); 10.11 (s, 1H, NH); 13C NMR (125.7 MHz, CDCl3) δ=29.51 (CH2), 38.34 (CH), 43.54 (CH2), 67.61 (CH2), 113.81 (aromatic-C), 118.68 (aromatic-C), 122.45 (aromatic-C), 126.84 (aromatic-C), 134.96 (aromatic-C), 138.77 (aromatic-C), 151.86 (C═O). Calculated (%) for C15H17F3N3O2 (328.13); C: 52.17, H: 5.25, N: 12.17. found (%); C: 52.08, H: 5.33, N: 12.07.

Sources & evidence

ORD record
ord-ff5b32ab0c5b4d939e63a4363ab75a34
Source dataset
uspto-grants-2015_07
Patent number
US09073900B2

Reaction notes

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