Trifluoroacetic acid → (4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-[1-(3-methyl-butyl)-piperidin-4-yl]-amine

HRID 1069180Notes

Reaction equation

HRID 1069180 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N1CCC(N(C2C=CC(OCC3C=CC=CC=3)=CC=2)[CH2:41][CH:42]=[C:43]([CH3:45])[CH3:44])CC1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:16]2[CH2:21][CH2:20][N:19]([CH2:41][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10641624(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amineHCID 107422094-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 9910060(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-[1-(3-methyl-butyl)-piperidin-4-yl]-amineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The preparation of (4-Benzyloxy-phenyl)-(3-methvl-but-2-enyl)-piperidin-4-yl-amine, (Ic): 4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 11.1 mmol) was dissolved in CH2Cl2 (20 mL) and treated with TFA (20 mL). The reaction was stirred for ten minutes, then concentrated in vacuo. The residue was redissolved in EtOAc (400 mL), then washed with saturated bicarbonate solution (2×400 mL) and brine (1×400 mL), dried over Na2SO4, and concentrated in vacuo to give 3.9 g (99%) of the desired product as a pale oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in EtOAc (400 mL)
  3. washwashed with saturated bicarbonate solution (2×400 mL) and brine (1×400 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bb534feb1114cb7b0a982a6780646b2
Source dataset
uspto-grants-2001_06
Patent number
US06251919B1

Reaction notes

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