Acetic Acid → HCID 59264610, compound

HRID 573480Notes

Reaction equation

HRID 573480 reaction equation
[CH3:1][C:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:16][C:17]([F:33])([F:32])[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:1][C:2]([N:9]1[CH2:14][CH2:13][CH:12]([NH:31][CH2:30][C:27]2[CH:26]=[CH:25][C:24]([C:21]3[CH:22]=[CH:23][C:18]([C:17]([F:16])([F:32])[F:33])=[CH:19][CH:20]=3)=[CH:29][CH:28]=2)[CH2:11][CH2:10]1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 37291554-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINEHCID 5049666Sodium triacetoxyborohydrideHCID 59264612Ethyl 2-methyl-2-(4-oxo-1-piperidinyl)propanoate

Product 1

HCID 59264610HCID 59264610, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of ethyl 2-methyl-2-(4-oxo-1-piperidinyl)propanoate (Int. A4) (25.6 g, 1.2 equiv), {[4′-(trifluoromethyl)-4-biphenylyl]methyl}amine (Int. A1) (31.1 g, 1.0 equiv), DCE (400 ml) and acetic acid (6.3 ml, 1.1 equiv) was stirred at room temperature under nitrogen. Sodium triacetoxyborohydride (33.5 g, 1.5 equiv) was added and stirring continued for 19 hours. Aqueous sodium carbonate (2M solution, excess) was added and stirred for 1.5 h, then the mixture was extracted with a mixture of diethyl ether and THF. The organic extracts were backwashed with water and brine, filterered through a pad of silica gel, dried over sodium sulfate and evaporated in vacuo. The desired product was obtained as a white solid (44.2 g) which was used without further purification.

Workup

  1. stirringstirring
  2. stirringstirred for 1.5 h
  3. extractionthe mixture was extracted with a mixture of diethyl ether and THF
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6bcdae324edc44bfb294c7b50b006e06
Source dataset
uspto-grants-2015_05
Patent number
US09029383B2

Reaction notes

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