Benzoic Acid → tert-Butyl 3-(benzoylamino)piperidine-1-carboxylate

HRID 1180973

Reaction equation

HRID 1180973 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.[NH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1>CN(C=O)C.C(N(CC)CC)C>[C:1]([NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1)(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 5458091-BOC-3-AminopiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22017033tert-Butyl 3-(benzoylamino)piperidine-1-carboxylateYield 39.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of benzoic acid (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-db2281eb53c3413ab6f05803a40067d7
Source dataset
uspto-grants-2007_10
Patent number
US07282497B2

Linked notes

Loading…