Acetic Acid → Rac-n-(1-isopropyl-3-phenyl-piperidin-3-yl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide

HRID 2177535Notes

Reaction equation

HRID 2177535 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[C:4]=1[C:5]([NH:7][C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1)=[O:6].C(O)(=O)C.[CH3:36][C:37]([CH3:39])=O.C([BH3-])#N.[Na+]>CO>[CH:37]([N:10]1[CH2:11][CH2:12][CH2:13][C:8]([NH:7][C:5](=[O:6])[C:4]2[C:20]([C:28]([F:31])([F:29])[F:30])=[CH:21][C:22]([C:24]([F:25])([F:26])[F:27])=[CH:23][C:3]=2[O:2][CH3:1])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1)([CH3:39])[CH3:36]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 59438392HCID 59438392, compound

Product 1

HCID 59438429Rac-n-(1-isopropyl-3-phenyl-piperidin-3-yl)-2-methoxy-4,6-bis-trifluoromethyl-benzamideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 35.7 mg (0.08 mmol) rac-2-methoxy-N-(3-phenyl-piperidin-3-yl)-4,6-bis-trifluoromethyl-benzamide in methanol were added 28 ul (0.48 mmol) acetic acid, 59 ul (0.8 mmol) acetone and finally 30 mg (0.4 mmol) sodium cyanoborohydride. The mixture was stirred at room temperature for 4 hours. The solvent was removed in vacuo. The residue was taken in ethyl acetate. The mixture was washed once with a 1N NaOH solution, once with water and once with brine. The aqueous layer was extracted once with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 33 mg (85%) of the title compound as a white foam. MS (m/e): 489.4 (M+H).

Workup

  1. customThe solvent was removed in vacuo
  2. washThe mixture was washed once with a 1N NaOH solution, once with water and once with brine
  3. extractionThe aqueous layer was extracted once with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-d0c5be45fda84f6295321e284db7b63d
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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