Trifluoroacetic acid → 1-Benzyl-1,2,3,4-tetrahydroquinolin-3-amine

HRID 2092170Notes

Reaction equation

HRID 2092170 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:16]1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO>[CH2:25]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:24][CH:15]([NH2:14])[CH2:16]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67236612Tert-butyl 1-benzyl-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Product 1

HCID 640312941-Benzyl-1,2,3,4-tetrahydroquinolin-3-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of (1-benzyl-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (481 mg, 1.42 mmol) in dichloromethane (6 mL), stirred for 30 minutes at ambient temperature, and concentrated. A solution of the resulting oil in methanol (10 mL) was treated with potassium carbonate (393 mg, 2.84 mmol), stirred for an hour at room temperature, and concentrated to afford the title compound as yellow residue. MS (DCI/NH3) m/z: 239.1 [M+H]+.

Workup

  1. concentrationconcentrated
  2. stirringstirred for an hour at room temperature
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b9b4f76b4c9f4a70ab9327bf1337f1c9
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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