N-Propylcyclohexanamine → HCID 178518607, compound

HRID 1007545Notes

Reaction equation

HRID 1007545 reaction equation
[CH:1]1(NCCC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:11]1([C:18]2[CH:27]=[CH:26][C:21]3[NH:22][C:23](=[O:25])[O:24][C:20]=3[CH:19]=2)[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1>>[CH:1]1([CH2:19][CH2:20][CH2:21][NH:22][C@H:14]2[CH2:15][CH2:16][C@H:11]([C:18]3[CH:27]=[CH:26][C:21]4[NH:22][C:23](=[O:25])[O:24][C:20]=4[CH:19]=3)[CH2:12][CH2:13]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 19178N-PropylcyclohexanamineHCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one

Product 1

HCID 178518607HCID 178518607, compoundYield 30.9%

Procedure

Condensation of cyclohexyl-1-propylamine (0.9 g, 6.4 mmol) and ketone 5 (1.5 g, 6.4 mmol), following the procedure described in Example 1, gave 6-{trans-4-[(3-cyclohexylpropyl)amino]cyclohexyl}-3H-benzoxazol-2-one (352 mg, 15%), as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 7.12 (br s, 1H), 6.97-6.93 (m, 2H), 3.70-3.10 (br s, 2H), 2.53 (t, J=7 Hz, 2H), 2.48-2.39 (m, 2H), 1.95 (br d, J=12 Hz, 2H), 1.77 (br d, J=12 Hz, 2H), 1.70-1.59 (m, 5H), 1.50-1.38 (m, 4H), 1.23-1.08 (m, 8H), 0.90-0.81 (m, 2H).

Sources & evidence

ORD record
ord-8e2605ef61c246e48ab7830e59923022
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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