Trifluoroacetic acid → (4-Cyclohexyl-piperidin-4-ylmethyl)-thiazol-2-yl-amine

HRID 1795173Notes

Reaction equation

HRID 1795173 reaction equation
FC(F)(F)C(O)=O.C(Cl)Cl.O.C(OC([N:19]1[CH2:24][CH2:23][C:22]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)([CH2:25][NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[CH2:21][CH2:20]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH:32]1([C:22]2([CH2:25][NH:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH2:21][CH2:20][NH:19][CH2:24][CH2:23]2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18672661TFA dichloromethane waterHCID 210237784-Cyclohexyl-4-(thiazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 22185363(4-Cyclohexyl-piperidin-4-ylmethyl)-thiazol-2-yl-amineYield 96%

Procedure

A ready-to-use solution of trifluoroacetic acid:methylene chloride:water (1:1:0.1, 7 mL) is added to 4-cyclohexyl-4-(thiazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl ester, 12, (312 mg, 0.82 mmol), and the reaction mixture is stirred for 0.5–1.0 hour. The mixture is then concentrated under reduced pressure and partitioned between aqueous sodium bicarbonate and ethyl acetate. The organics are separated and the solvent removed under reduced pressure. The crude product is purified by preparative HPLC to afford 220 mg (96% yield) of the desired compound as the trifluoroacetic acid salt.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. custompartitioned between aqueous sodium bicarbonate and ethyl acetate
  3. customThe organics are separated
  4. customthe solvent removed under reduced pressure
  5. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-f70e9d9bf66c4adc981924b61c422136
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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