Methanol → Methyl (piperidin-4-yl)acetate--hydrogen chloride (1/1)

HRID 902643Notes

Reaction equation

HRID 902643 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([OH:11])=[O:10])[CH2:4][CH2:3]1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[CH3:16][O:10][C:9](=[O:11])[CH2:8][CH:5]1[CH2:6][CH2:7][NH:2][CH2:3][CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 155657754-Piperidineacetic acid hydrochloride

Product 1

HCID 18423605Methyl (piperidin-4-yl)acetate--hydrogen chloride (1/1)

Conditions

Temperature
40 °C

Procedure

To a stirring suspension of piperidin-4-yl-acetic acid hydrochloride in MeOH (15 mL) at −5° C. was added thionyl chloride (1.12 mL, 15.3 mmol) dropwise. The reaction mixture was allowed to reach to RT then heated to 40° C. for 4 h. The reaction mixture was concentrated in vacuo and the resulting white solid was azeotroped with toluene twice. Washed with ether and filtered to give 2.7 g (quantitative yield). MS(ESI) 158.2 (M+H+).

Workup

  1. customto reach to RT
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting white solid was azeotroped with toluene twice
  4. washWashed with ether
  5. filtrationfiltered
  6. customto give 2.7 g (quantitative yield)

Sources & evidence

ORD record
ord-e2dceb923a404c33944a2787678ee724
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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