Trifluoroacetic acid → HCID 86643200, compound

HRID 2389544Notes

Reaction equation

HRID 2389544 reaction equation
[C:1]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH:9]([NH:17]C(=O)OC(C)(C)C)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>ClCCl>[OH:29][C:27]([C:26]([F:31])([F:30])[F:25])=[O:28].[C:1]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH:9]([NH2:17])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59400240HCID 59400240, compound

Product 1

HCID 86643200HCID 86643200, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 1-phenyl-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (375 mg, 1.16 mmol) in dichloromethane (4 mL) was treated with trifluoroacetic acid (2 mL) at ambient temperature for 3 hours. The solvent was removed under reduced pressure and diethylether added. The solid that formed was filtered and dried to give 1-phenyl-1,2,3,4-tetrahydroquinolin-3-amine TFA salt as a yellow solid (350 mg). M.p.=201-203° C. 1H NMR (DMSO) 400 MHz δ 8.13 (s, br, 2H), 7.46 (m, 2H), 7.34 (m, 2H), 7.23 (m, 2H), 7.15 (m, 1H), 6.99 (m, 1H), 6.77 (dt, J=1.2 and 7.6 Hz, 1H), 6.59 (m, 1H), 3.86 (m, br, 2H), 3.56 (m, 1H), 3.27 (m, 1H), 2.90 (dd, J=5.2 and 12 Hz, 1H). LCMS m/e 225 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure and diethylether
  2. additionadded
  3. customThe solid that formed
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-65a29ea32b3d47fab94d260620b133cb
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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