Triethylamine → HCID 178525692, compound

HRID 1713827Notes

Reaction equation

HRID 1713827 reaction equation
C(N(CC)CC)C.Cl[C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1>CO.[Pd]>[C:12]1([C@H:15]2[CH2:16][CH2:17][C@H:18]([C:21]([OH:23])=[O:22])[CH2:19][CH2:20]2)[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 178525692HCID 178525692, compoundYield 124.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Palladium (10 wt. %) on carbon (50 g) and triethylamine (90 mL, 0.65 mol) were added sequentially, each in one portion, to a stirred solution of 4-(4-chlorophenyl)cyclohexanecarboxylic acid (150 g, 0.63 mol) in MeOH (1.5 L). The reaction mixture was stirred under a hydrogen atmosphere for 4 h at 50° C. at a pressure of 5 bar then cooled, filtered and then concentrated in vacuo to give the title compound (160 g, 83%) as a solid, which was contaminated with triethylamine hydrochloride (0.65 mol) and used with no further purification; 1H NMR δ 1.23 (9H, t), 1.44-1.53 (4H, m), 1.8-1.9 (2H, m), 1.96-2:05 (2H, m), 2.22-2.32 (1H, m), 2.45-2.58 (1H, m), 3.05 (6H, q), 7.1-7.35 (5H, m).

Workup

  1. temperaturethen cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf26488c2b694450b7a76cfbef608576
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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