N-Methylethylamine → HCID 68674635, compound

HRID 333235Notes

Reaction equation

HRID 333235 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][CH3:21])[CH3:19]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([N:20]([CH2:18][CH3:19])[CH3:21])=[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 12219N-MethylethylamineHCID 594622HCID 594622, compound

Product 1

HCID 68674635HCID 68674635, compoundYield 30%

Procedure

The amide was synthesized from 1-(3,4-dichlorophenyl)-cyclohexanecarboxylic acid (390 mg, 1.43 mmol) and ethylmethylamine using General Procedure G and was isolated in 30% yield as a white solid. HPLC Rt=11.66 min; 1H NMR (400 mHz, CDCl3) 7.40-7.30 (m, 2H), 7.10 (dd, J=2.2, 8.4 Hz, 1H), 3.31 (bs, 2H), 2.59 (bs, 3H), 2.30 (d, J=12.5 Hz, 2H), 1.76-1.55 (m, 7H), 1.32-1.25 (m, 2H), 1.00 (bs, 3H); 13C NMR (100 mHz, CDCl3) 147.0, 132.9, 130.8, 130.3, 127.5, 125.2, 51.0, 44.5, 36.8, 25.9, 23.5; GC-MS (SCOUT) 13.01 min, M+ 313.

Workup

  1. customwas isolated in 30% yield as a white solid
  2. customGC-MS (SCOUT) 13.01 min, M+ 313

Sources & evidence

ORD record
ord-3229ed333e924b6597d2040e8a03e93b
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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