1,2-Dichloroethane → N-piperidin-1-yl-butyramide

HRID 1830189Notes

Reaction equation

HRID 1830189 reaction equation
O=C([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)CC(CS(CC1C=CC=CC=1)(=O)=O)C(O)=O.OC(C(F)(F)F)=O.N[CH:33]([CH2:45]C)[CH:34]([C:36]1[O:37]C2C=CC=CC=2[N:40]=1)O.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[N:19]1([NH:40][C:36](=[O:37])[CH2:34][CH2:33][CH3:45])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220539604-Oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyric acidHCID 866023552-amino-1-benzooxazol-2-yl-butan-1-ol TFA salt

Product 1

HCID 17164277N-piperidin-1-yl-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyric acid (141 mg, 0.4 mmol), 2-amino-1-benzooxazol-2-yl-butan-1-ol TFA salt. (129 mg), prepared as in reference 20, and HOBt (74 mg, 0.48 mmol) in MeCl2 (5 mL), was added EDC (115 mg, 0.6 mmol) and N-methylmorpholine (0.25 ml) at room temperature. After stir-ring for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried with MgSO4 and concentrated to yield 157 mg of N-piperidin-1-yl-butyramide. Without further purification, the crude product was used for next reaction; MS: 540.4(M−1), 542.6(M+1).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7ceb6f682914418e8e9a590d64b28c26
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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