Oxalyl chloride → Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

HRID 1854310Notes

Reaction equation

HRID 1854310 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl.CN(C=O)C>[Cl:23][C:17]([CH:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12][CH2:13]1)=[O:19]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid (4.50 g, 17.1 mmol, Preparation #5, Step A) in DCM (40 mL) at ambient temperature was added oxalyl chloride (3.00 mL, 34.2 mmol) followed by DMF (0.10 mL, 1.3 mmol). After about 3 h, the reaction was concentrated under reduced pressure to constant weight to afford benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate as a yellow oil (3.88 g, 81%): 1H NMR (CDCl3) δ 7.44-7.35 (m, 5H), 5.16 (s, 2H), 4.20-4.10 (m, 2H), 3.03-2.89 (m, 3H), 2.15-2.05 (m, 2H), 1.81-1.76 (m, 2H).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure to constant weight

Sources & evidence

ORD record
ord-8db0aae778a74813b5bfd73d18d374a6
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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