Pyridine → HCID 68779529, compound

HRID 2061575Notes

Reaction equation

HRID 2061575 reaction equation
[NH2:1][C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.N1C=CC=CC=1.[Cl:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[CH3:18][O:17][C:15]([C:2]1([NH:1][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][Cl:25])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:6][CH2:7]1)=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 208719401-tert-Butyl 4-methyl 4-aminopiperidine-1,4-dicarboxylate

Product 1

HCID 68779529HCID 68779529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of methyl 4-amino-1-BOC-piperidine-4-carboxylate (2.0 g, 6.78 mmol) in DCM (15 mL) and pyridine (2.10 mL, 20.35 mmol), 4-chlorobutyryl chloride (0.84 mL, 7.5 mmol) in DCM (5 mL) was added slowly at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 16 hours. The reaction mixture was diluted with DCM (40 mL), and quenched with saturated NaHCO3 (30 mL). The organic layer was separated and the aqueous layer was extracted twice with DCM. The combined organic layers were then washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated to give 4-(4-chloro-butyrylamino)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester which was used further without purification.

Workup

  1. customquenched with saturated NaHCO3 (30 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with DCM
  4. washThe combined organic layers were then washed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-daf5dae3277d4371b6397db62cdf17c3
Source dataset
uspto-grants-2012_10
Patent number
US08283357B2

Reaction notes

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