Hydrochloric Acid → HCID 53970063, compound

HRID 494019Notes

Reaction equation

HRID 494019 reaction equation
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([OH:23])=O)[CH2:17][CH2:16]1.Cl>ClCCl.C(N(CC)CC)C>[O:11]=[CH:12][CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:9][CH2:5][C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:23])[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 19748285HCID 19748285, compound

Product 1

HCID 53970063HCID 53970063, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-60 °C

Procedure

0.81 ml of dimethylsulphoxide in solution in 10 ml of dichloromethane (DCM) is cooled to −50° C. and 0.42 ml (4.8 mM) of oxalyl chloride in solution in 1.5 ml of DCM are added. The mixture is agitated for 10 minutes at −60° C. are then, at this temperature, 1.21 g (4.4 mM) of the benzyl ester of 4-(3-hydroxypropyl)piperidinecarboxylic acid in solution in 6 ml of DCM are added dropwise. The reaction mixture is agitated for 30 minutes at −50° C. and 3 ml of triethylamine are then added dropwise and the temperature is allowed to rise up to ambient temperature in 2 hours. The mixture is hydrolysed on 25 ml of N hydrochloric acid and extracted with DCM. The organic phase is washed with water, dried over magnesium sulphate and concentrated under reduced pressure. The crude product is purified by silica gel chromatography in eluting with the aid of a cyclohexane/ethyl acetate mixture (75/25; v/v). The product sought after is thus obtained as a yellow oil (yield=83%).

Workup

  1. stirringThe reaction mixture is agitated for 30 minutes at −50° C.
  2. waitto rise up to ambient temperature in 2 hours
  3. extractionextracted with DCM
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by silica gel chromatography
  8. washin eluting with the aid of a cyclohexane/ethyl acetate mixture (75/25; v/v)

Sources & evidence

ORD record
ord-aee8ccc4d15f4f69bb0414b50abb71da
Source dataset
uspto-grants-2009_05
Patent number
US07538111B2

Reaction notes

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