Methanol → Methyl 3-(piperidin-4-yl)propanoate hydrochloride

HRID 511176Notes

Reaction equation

HRID 511176 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.S(Cl)([Cl:21])=O.[CH3:23]O>>[ClH:21].[CH3:23][O:18][C:16](=[O:17])[CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

Product 1

HCID 49761244Methyl 3-(piperidin-4-yl)propanoate hydrochloride

Procedure

To a solution of 4-(2-carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (1.95 g; 7.58 mmol) in methanol (5 mL) is slowly added thionylchloride (0.99 g; 8.34 mmol) and the reaction mixture is stirred at room temperature for 30 minutes. All volatiles are then removed under high vacuum and the resulting residue triturated with diethyl ether, sucked to dryness and washed (diethyl ether) to afford the desired compound (1.49 g; 7.18 mmol).

Workup

  1. customAll volatiles are then removed under high vacuum
  2. customthe resulting residue triturated with diethyl ether
  3. washwashed (diethyl ether)

Sources & evidence

ORD record
ord-a747ce24015c4862a78853eaa16eb76e
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

Loading…