Diethylamine → 1-(3,4-Dichlorophenyl)-N,N-diethylcyclohexanecarboxamide

HRID 333231Notes

Reaction equation

HRID 333231 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 594622HCID 594622, compound

Product 1

HCID 686738801-(3,4-Dichlorophenyl)-N,N-diethylcyclohexanecarboxamideYield 13%

Procedure

The amide was synthesized from 1-(3,4-dichlorophenyl)-cyclohexanecarboxylic acid (232 mg, 0.85 mmol) and diethyl amine using General Procedure G and was isolated in 13% yield as a white solid. HPLC Rt=12.0 min; 1H NMR (400 mHz, CDCl3) 7.38-7.26 (m, 2H), 7.08 (dd, J=2.2, 8.4 Hz, 1H), 3.29 (bs, 2H), 2.84 (bs, 2H), 2.26 (d, J=12.1 Hz, 2H), 1.73-1.54 (m, 7H), 1.29-1.24 (m, 2H), 1.08 (bs, 3H), 0.82 (bs, 3H); 13C NMR (100 mHz, CDCl3) 172.9, 147.2, 133.0, 130.8, 130.4, 127.5, 125.2, 51.2, 42.0, 40.9, 37.3, 26.0, 23.7, 13.4, 12.4; GC-MS (SCOUT) 13.2 min, M+ 327.

Workup

  1. customwas isolated in 13% yield as a white solid
  2. customGC-MS (SCOUT) 13.2 min, M+ 327

Sources & evidence

ORD record
ord-af387ea98147459c977f330521cdd39e
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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