6-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one → HCID 178457494, compound

HRID 1007546Notes

Reaction equation

HRID 1007546 reaction equation
[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH2:4].[CH:12]1([C:19]2[CH:28]=[CH:27][C:22]3[NH:23][C:24](=[O:26])[O:25][C:21]=3[CH:20]=2)[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>>[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH:4][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:19]2[CH:28]=[CH:27][C:22]3[NH:23][C:24](=[O:26])[O:25][C:21]=3[CH:20]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-oneHCID 12672558beta-Methylbenzenepropanamine

Product 1

HCID 178457494HCID 178457494, compoundYield 48%

Procedure

Condensation of 2-methyl-3-phenylpropylamine (830 mg, 3.97 mmol) and ketone 5 (918 mg, 3.97 mmol), following the procedure described in Example 1, gave compound 6-{trans-[4-(2-methyl-3-phenylpropylamino)-cyclohexyl]}-3H-benzoxazol-2-one (400 mg, 48%): 1H NMR (500 MHz, DMSO-d6): δ 7.32-7.21 (m, 2H), 7.19-7.17 (m, 4H), 7.03-6.98 (m, 2H), 2.77 (dd, J=13, 6 Hz, 1H), 2.55-2.34 (m, 7H), 1.99-1.97 (m, 2H), 1.84-1.80 (m, 2H), 1.50-1.47 (m, 2H), 1.18-1.05 (m, 2H), 0.88 (d, J=6 Hz, 3H).

Sources & evidence

ORD record
ord-0fe88c0492ee49259654ae8724f7861f
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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