Trifluoroacetic acid → HCID 53725158, compound

HRID 1069454Notes

Reaction equation

HRID 1069454 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:22][CH:21]=2)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC1C=CC([N:48]([CH2:55][CH2:56][CH:57]([CH3:59])[CH3:58])C2CCNCC2)=CC=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:48][C@@H:55]([CH2:56][CH:57]([CH3:59])[CH3:58])[C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:24][CH:25]=2)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:12][CH2:13]1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69969559HCID 69969559, compound

Product 1

HCID 53725158HCID 53725158, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The preparation of (4-Benzyloxy-phenyl)-(3-methyl-butyl)-piperidin-4yl-amine 4-[(4-Benzyloxy-phenyl)-(3-methyl-butyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (3.27 g, 7.22 mmol) was dissolved in CH2Cl2 (25 mL), treated with TFA (25 mL), and stirred for 30 minutes. The reaction was concentrated, diluted with EtOAc (300 mL), washed twice with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated to give 2.62 g of the desired product.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with EtOAc (300 mL)
  3. washwashed twice with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-41c214b03568416e9b5241eb6601111a
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

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