Dimethylformamide → tert-Butyl 3-(benzoylamino)piperidine-1-carboxylate

HRID 7282

Reaction equation

HRID 7282 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH:13]1[CH:14]=[CH:15][C:16]2N(O)N=N[C:17]=2[CH:18]=1.C(N(CC)CC)C.[NH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]1.CN([CH:47]=[O:48])C>>[C:47]([NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]1)(=[O:48])[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:18]=1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5458091-BOC-3-AminopiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22017033tert-Butyl 3-(benzoylamino)piperidine-1-carboxylate

Procedure

A solution of benzoic add (0.123 g) in DMF (5 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.231 g), HOBT (0.163 g) and triethylamine (0.56 ml) and stirred at room temperature for 1 h. A solution of 3-amino-1-N-Boc-piperidine (0.3 g) in DMF (1 ml) was then added and stirring continued for 18 h. The solution was concentrated under reduced pressure to give an oil which was partitioned between ethyl acetate and water. The separated organic extracts were washed with water, hydrochloric acid (2N), saturated sodium bicarbonate solution and brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (0.120 g) as a yellow solid.

Workup

  1. stirringstirring
  2. waitcontinued for 18 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. customto give an oil which
  5. customwas partitioned between ethyl acetate and water
  6. washThe separated organic extracts were washed with water, hydrochloric acid (2N), saturated sodium bicarbonate solution and brine
  7. dry with materialdried (over magnesium sulphate)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1e715609e01411ba597fa73de2bd029
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Linked notes

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