Trifluoroacetic acid → HCID 68809786, compound

HRID 434292Notes

Reaction equation

HRID 434292 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@H:8]([CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([C:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:24])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68811023HCID 68811023, compound

Product 1

HCID 68809786HCID 68809786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(R)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-pyridin-3-ylmethyl-ethyl}-carbamic acid tert-butyl ester (0.149 g, 0.34 mmol) in dichloromethane (2 ml) is added trifluoroacetic acid (0.5 ml) and the reaction mixture stirred at ambient temperature for 1 hour. The reaction mixture is evaporated and the residue takeup in hydrochloric acid (1M), the solution basified with sodium hydroxide solution (4M) and the precipitate extracted into dichloromethane. The dichloromethane was dried over magnesium sulphate and evaporated to afford [1-((R)-2-amino-3-pyridin-3-yl-propyl)-piperidin-4-yl]-(4-fluoro-phenyl)-methanone. 1H NMR (400 MHz, CDCl3) δ 1.63-1.85 (m 4H), 1.88-2.00 (m 1H), 2.08-2.32 (m 5H), 2.50 (dd J 13.5 7.9 1H), 2.67 (dd J 13.5 4.9 1H), 2.78-2.98 (m, 2H), 3.04-3.20 (m, 2H), 7.04 (t J 8.8 2H), 7.17 (dd J 6.9 4.9 1H) 7.48 (d J 7.9 1H), 7.88 (dd, J 8.8 5.4 2H), 8.33-8.45 (m, 2H).

Workup

  1. customThe reaction mixture is evaporated
  2. extractionthe precipitate extracted into dichloromethane
  3. dry with materialThe dichloromethane was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-5700fd3050874261acc1a08ccbb47fdc
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Reaction notes

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