Ethylamine → HCID 68674973, compound

HRID 333237Notes

Reaction equation

HRID 333237 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]([NH2:20])[CH3:19]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([NH:20][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 6341EthylamineHCID 594622HCID 594622, compound

Product 1

HCID 68674973HCID 68674973, compoundYield 28%

Procedure

The amide was synthesized from 1-(3,4-dichlorophenyl)-cyclohexanecarboxylic acid (280 mg, 1.03 mmol) and ethylamine using General Procedure G and was isolated in 28% yield as a white solid. HPLC Rt=10.61 min; 1H NMR (400 mHz, CDCl3) 7.44 (d, J=2.2 Hz, 1H), 7.37 (d, J=8.43 Hz, 1H), 7.21 (dd, J=2.2, 8.4 Hz, 1H), 5.4 (bs, 1H), 3.21-3.14 (m, 2H), 2.25-2.20 (m, 2H), 1.86-1.79 (m, 2H), 1.58-1.52 (m, 5H), 1.35-1.32 (m, 1H), 1.00 (at, 3H); 13C NMR (100 mHz, CDCl3) 174.3, 144.8, 132.8, 130.9, 130.7, 128.7, 126.2, 50.5, 34.8, 34.7, 25.7, 23.0, 14.8; GC-MS (SCOUT) 12.9 min, M+ 299.

Workup

  1. customwas isolated in 28% yield as a white solid
  2. customGC-MS (SCOUT) 12.9 min, M+ 299

Sources & evidence

ORD record
ord-a84a6beb1a7b470aa266db9bc856d03c
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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