Chloroacetyl chloride → HCID 66564635, compound

HRID 1619338Notes

Reaction equation

HRID 1619338 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(C(C)C)CC)(C)C.[Cl:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl>[Cl:25][CH2:26][C:27]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:28]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 66564635HCID 66564635, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(aminomethyl)piperidine-1-carboxylate (2.0 g, 9.3 mmol) and diisopropylethylamine (5 mL) in DCM (30 mL) was added 2-chloroacetyl chloride (1.2 g, 10.6 mmol) dropwise at 0° C. The mixture was stirred at room temperature overnight. Then the mixture was quenched with water (30 mL) and extracted with DCM (5×100 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was used directly for the next reaction. MS (ESI): 291, 293 (MH+).

Workup

  1. customThen the mixture was quenched with water (30 mL)
  2. extractionextracted with DCM (5×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was used directly for the next reaction

Sources & evidence

ORD record
ord-b81dfa0c7b5b432f8b4d24e7bb7a8cdd
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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