Acetic Anhydride → HCID 178474714, compound

HRID 896638Notes

Reaction equation

HRID 896638 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[OH:23][C:20]1[CH:19]=[CH:18][C:17]([C@H:14]2[CH2:13][CH2:12][C@H:11]([N:10]([CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:24](=[O:26])[CH3:25])[CH2:16][CH2:15]2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178516054HCID 178516054, compound

Product 1

HCID 178474714HCID 178474714, compound

Procedure

In a manner similar to Example 16, trans-4-[4-(3-phenylpropylanino)cyclohexyl]phenol was allowed to react with acetic anhydride to give trans-N-[4-(4-hydroxyphenyl)cyclohexyl]-N-(3-phenylpropyl) acetamide. Yield (90 mg, 2%): mp 175-180° C.; IR (KBr): 3240, 2929, 1620, 1590 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 9.11 (s, 1H), 7.30-7.17 (m, 5H), 7.00 (d, J=9 Hz, 2H), 6.69 (dd, J=9, 2 Hz, 2H), 3.37 (m, 1H), 3.25 (m, 4H), 2.61 (m, 2H), 2.41 (m, 1H), 2.10 (s, 3H), 1.87-1.75 (m, 4H), 1.72-1.46 (m, 4H); CI-MS (methane) (m/z): 352 [M+H]+; HRMS-API (m/z): [M+H]+ Calcd for C23H29NO2, 352.2276. found: 352.2278. HPLC: method A, 12.08 minutes (97.3%); method B, 16.36 minutes (98.9%); Anal. Calcd for C23H29NO2.0.75H2O: C, 75.67; H, 8.43; N, 3.84. Found: C, 75.40; H, 7.93; N, 3.78.

Sources & evidence

ORD record
ord-a6582820e5f7456cb7fdbcd28611dc05
Source dataset
uspto-grants-2005_07
Patent number
US06919377B2

Reaction notes

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