Triethylamine → Methyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate

HRID 922132Notes

Reaction equation

HRID 922132 reaction equation
[NH2:1][C:2]1([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:6][C:5]([O:12][CH3:13])([C:8]([F:11])([F:10])[F:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:36])=[C:30]([CH2:32][C:33](Cl)=[O:34])[CH:31]=1>ClCCl>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:36])=[C:30]([CH2:32][C:33]([NH:1][C:2]2([C:14]([O:16][CH3:17])=[O:15])[CH2:3][CH2:4][C:5]([O:12][CH3:13])([C:8]([F:11])([F:10])[F:9])[CH2:6][CH2:7]2)=[O:34])[CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 51063875(5-Bromo-2-methylphenyl)acetyl chlorideHCID 71246475Methyl 1-amino-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate

Product 1

HCID 71246345Methyl 1-{[(5-bromo-2-methylphenyl)acetyl]amino}-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3.00 g (11.75 mmol) of methyl 1-amino-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate (Example 22A) and 1.19 g (11.75 mmol) of triethylamine were dissolved in 40 ml of dichloromethane. 2.65 g (10.69 mmol) of (5-bromo-2-methylphenyl)acetyl chloride (Example 3A), dissolved in 40 ml of dichloromethane, were added dropwise to this solution, and the reaction mixture was stirred at room temperature overnight. For work-up, the mixture was diluted with dichloromethane and the organic phase was washed with aqueous saturated sodium bicarbonate solution and with aqueous 1% strength citric acid. After drying over sodium sulphate, the organic phase was concentrated and the product was dried. This gave 4.79 g (87% of theory) of the title compound as a beige powder.

Workup

  1. additionwere added dropwise to this solution
  2. washthe organic phase was washed with aqueous saturated sodium bicarbonate solution and with aqueous 1% strength citric acid
  3. dry with materialAfter drying over sodium sulphate
  4. concentrationthe organic phase was concentrated
  5. customthe product was dried

Sources & evidence

ORD record
ord-fd313bcc152b416798b912c498ea9f73
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

Loading…