Trifluoroacetic acid → Trifluoroacetic acid

HRID 419428Notes

Reaction equation

HRID 419428 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)C.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]>C(Cl)Cl>[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31].[F:33][C:32]([F:35])([F:34])[C:30]([OH:36])=[O:31].[F:33][C:32]([F:35])([F:34])[C:30]([OH:36])=[O:31].[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:18][CH2:19]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18971584Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 86625193Phenylmethyl 4-(4-piperidinyl)-1-piperazinecarboxylate bis(trifluoroacetate) salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Phenylmethyl 4-(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinyl)-1-piperazinecarboxylate from previous step was dissolved in DCM (60 mL) and cooled to 0° C. TFA (20 mL) was added. Reaction was stirred for 1 h. TLC showed no starting material remaining. Removed DCM and TFA on rotovap to give title compound of step B (presumed to be the bis-TFA salt) (14.0 g, 53% over 2 steps) which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.03-7.40 (m, 5H), 5.02 (s, 2H), 2.93-4.16 (m, 7H), 2.11-2.82 (m, 7H), 1.06-1.88 (m, 4H).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-54d2b45fa18a40bb8f3ba70ab928ba9a
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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