1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → HCID 86631298, compound

HRID 1260925Notes

Reaction equation

HRID 1260925 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@H:10]2[C@H:15]([N:16]([CH3:33])[C:17](=[O:32])[C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=3)[CH2:14][CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[C:34]([N:41]1[CH2:49][CH2:48][CH:44]([C:45](O)=[O:46])[CH2:43][CH2:42]1)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O>[F:27][C:24]([F:25])([F:26])[C:22]1[CH:23]=[C:18]([C:17]([N:16]([CH3:33])[C@@H:15]2[CH2:14][CH2:13][N:12]([C:45]([CH:44]3[CH2:48][CH2:49][N:41]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:42][CH2:43]3)=[O:46])[CH2:11][C@H:10]2[C:5]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=2)=[O:32])[CH:19]=[C:20]([C:28]([F:31])([F:29])[F:30])[CH:21]=1

Participants

6

Reactant 2

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 86631295HCID 86631295, compound

Product 1

HCID 86631298HCID 86631298, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 757711-HydroxybenzotriazoleCatalystHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of N-[(3R*,4R*)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide monohydrochloride (0.90 g) obtained in Example 2, N-Boc-isonipecotic acid (1.52 g), WSC.HCl (0.82 mg) and HOBt (0.65 mg) was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane, then 0→10% methanol/ethyl acetate) to give the title compound (1.19 g, 59%) as a white powder.

Workup

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient

Sources & evidence

ORD record
ord-21f40dc9d9474169a0f23f20fd380248
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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