Trifluoroacetic acid → HCID 18353721, compound

HRID 430078Notes

Reaction equation

HRID 430078 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH:14]=[CH:13][CH2:12][N:11]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[CH2:16][N:11]1[CH2:12][CH:13]=[CH:14][CH2:15][CH:10]1[CH2:9][CH2:8][NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53896748HCID 53896748, compound

Product 1

HCID 18353721HCID 18353721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(3,4-dichlorobenzyl)-1,2,3,6-tetrahydropyridin-2-yl]ethylcarbamic acid tert-butyl ester (1.0 g, 2.9 mmol) dissolved in dichloromethane at 5° C. was added trifluoroacetic acid (10 mL). After stirring at room temperature for 2.5 h the solvent was evapaorated, partitioned between dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (25 mL). The organic layer was separated, dried and evaporated to yield the title compound as a colourless gum. δH (CDCl3+D2O) 1.46-1.63 (1H, m), 1.71-1.95 (2H, m), 2.18-2.47 (1H, m), 2.68-3.07 (4H, m), 3.60 (2H, s), 5.30 (1H, s), 5.57 (1H, d, J=10.1 Hz), 5.74 (1H, d, J=10.2 Hz), 7.10-7.50 (3H, m); MS (ES+) 285 (100%) MH+.

Workup

  1. custompartitioned between dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (25 mL)
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-8b35f6dd0f3445c2a5d7803f472803fb
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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