Water → Tert-butyl 4-(acetamidomethyl)piperidine-1-carboxylate

HRID 1864136Notes

Reaction equation

HRID 1864136 reaction equation
CCN(CC)CC.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH2:22])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[C:23](Cl)(=[O:25])[CH3:24].O>C1COCC1>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 18924095Tert-butyl 4-(acetamidomethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 32 mL reaction vial was placed a stir bar, Et3N (0.5 mL) and 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.3 g) dissolved in 10 mL anhydrous THF. Acetic acid chloride (0.48 g) was added dropwise through a syringe at 0° C. The mixture was stirred 2 hrs at room temperature. After worked up with H2O at 0° C., it was extracted with EtOAc. The organic extracts were washed with 2M NaOH solution, NaHSO4 and saturated NaCl solution. After dried over Na2SO4, it was concentrated to give crude 4-(acetylamino-methyl)-piperidine-1-carboxylic acid tert-butyl ester. 1H NMR (CDCl3, 400 MHz) δ 1.14 (m, 2H), 1.45 (s, 9H), 1.65 (m, 2H), 1.68 (m, 1H), 1.99 (s, 3H), 2.66 (m, 2H), 3.14 (m, 2H), 4.12 (m, 2H), 5.51 (m, 1H). Exact mass calculated for C13H24N2O3 256.18, found 257.4 (MH+).

Workup

  1. customIn a 32 mL reaction
  2. extractionit was extracted with EtOAc
  3. washThe organic extracts were washed with 2M NaOH solution, NaHSO4 and saturated NaCl solution
  4. dry with materialAfter dried over Na2SO4, it
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-33ac6e92221e4f1d90a32d0bfa2d0edd
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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