Acetic Anhydride → tert-Butyl (1-acetylpiperidin-4-yl)carbamate

HRID 2202079Notes

Reaction equation

HRID 2202079 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.CCN(CC)CC.[CH3:22][C:23](OC(C)=O)=[O:24]>C(Cl)Cl>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:23](=[O:24])[CH3:22])[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 22741830tert-Butyl (1-acetylpiperidin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl piperidin-4-ylcarbamate (200 g, 1 mol) and Et3N (150 g, 1.5 mol) in DCM (3000 mL) was added Ac2O (102 g, 1 mol) dropwise over 1 h, while maintained the temperature at 0° C. After addition, the mixture was stirred 0° C. for another 2 h, at which time TLC showed the reaction was completed. The solution was quenched by addition of water (1 L). The organic phase was collected and washed with saturated aqueous NaHCO3 (1 L), dried (Na2SO4) and concentrated to give crude product. Four batches were run in parallel and produced a combined crude product weight of 670 g. This crude was used directly in the step. LCMS (m/z): 243.1 (M+1).

Workup

  1. additionAfter addition
  2. customThe solution was quenched by addition of water (1 L)
  3. customThe organic phase was collected
  4. washwashed with saturated aqueous NaHCO3 (1 L)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give crude product

Sources & evidence

ORD record
ord-a3884957cdff4ef0b32ae3adbf2b9e83
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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