Dimethylformamide → 1-Piperidinecarboxamide

HRID 257544Notes

Reaction equation

HRID 257544 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.C[N:18]([CH:20]=[O:21])C>>[N:1]1([C:20]([NH2:18])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 728871-Piperidinecarboxamide

Procedure

Combine N-(t-butoxycarbonyl)-S-methionine (1.50 g, 6.0 mmol), piperidine (0.51 g, 6.0 mmol) and HOBT (0.91 g, 6.0 mmol) in DMF (40 ml). Add DEC (1.15 g, 6.0 mmol). Stir 5 hours, concentrate in vacuo, and partition between EtOAc and H2O. Wash with aqueous NaHCO3, dry, and concentrate to obtain the piperidine amide as a colorless oil (TLC single spot Rf =0.6 in 5% MeOH/CH2Cl2).

Workup

  1. concentrationconcentrate in vacuo
  2. custompartition between EtOAc and H2O
  3. washWash with aqueous NaHCO3
  4. customdry
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-ee93bd3e81114f3ea5b22cfa20286701
Source dataset
uspto-grants-1993_11
Patent number
US05262436

Reaction notes

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