Dimethylamine → HCID 68673029, compound

HRID 333232Notes

Reaction equation

HRID 333232 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].[CH3:18][NH:19][CH3:20]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([N:19]([CH3:20])[CH3:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 594622HCID 594622, compound

Product 1

HCID 68673029HCID 68673029, compoundYield 36%

Procedure

The amide was synthesized from 1-(3,4-dichlorophenyl)-cyclohexanecarboxylic acid (182 mg, 0.67 mmol) and dimethyl amine using General Procedure G and isolated in 36% yield as a white solid. HPLC Rt=11.27 min; 1H NMR (400 mHz, CDCl3) 7.36-7.34 (m, 2H), 7.06 (dd, J=2.2, 8.4 Hz, 1H), 2.71 (bs, 6H), 2.29 (d, J=12.1 Hz, 2H), 1.68-1.53 (m, 7H), 1.25-1.21 (m, 2H); 13C NMR (100 mHz, CDCl3) 173.9, 146.9, 133.0, 130.9, 130.4, 127.4, 125.2, 51.0, 38.1, 36.7, 25.9, 23.6; GC-MS (SCOUT) 12.8 min, M+ 299.

Workup

  1. customisolated in 36% yield as a white solid
  2. customGC-MS (SCOUT) 12.8 min, M+ 299

Sources & evidence

ORD record
ord-e26af291484248c0a8a3bd45a9485f75
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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