Trifluoroacetic acid → HCID 22279508, compound

HRID 1063375Notes

Reaction equation

HRID 1063375 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][Cl:19])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:19][CH2:18][CH2:17][CH2:16][C:15]#[C:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69783571HCID 69783571, compound

Product 1

HCID 22279508HCID 22279508, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14.6 g (16.3 mmol) of the crude 4-(5-Chloro-pent-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester in 44 ml CH2Cl2 was treated with 44 ml of TFA at 0° C. (for 20 min). The reaction was evaporated and partitioned between aqueous 10% KHSO4/Et2O (3×). The aqueous phase was adjusted to pH>10 by adding 1N NaOH and extracted with EtOAc (3×) The organic phase was dried over Na2SO4 and evaporated to give 1.41 g (50% over two steps) of 4-(5-Chloro-pent-1-ynyl)-piperidine, MS: 186 (MH+, 1Cl).

Workup

  1. customThe reaction was evaporated
  2. custompartitioned between aqueous 10% KHSO4/Et2O (3×)
  3. additionby adding 1N NaOH
  4. extractionextracted with EtOAc (3×) The organic phase
  5. dry with materialwas dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-b68145ce8089434f8606e74bffa4bab3
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

Loading…