Triethylamine → (trans)-Ethyl 4-[[[(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)carbonyl]-amino]methyl]-3-ethoxy-1-piperidinecarboxylate

HRID 1264657Notes

Reaction equation

HRID 1264657 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]([OH:21])=O)[C:12]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:18]=1.ClC(OCC)=O.[NH2:28][CH2:29][C@@H:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][C@H:31]1[O:41][CH2:42][CH3:43]>C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]([NH:28][CH2:29][C@@H:30]2[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][C@H:31]2[O:41][CH2:42][CH3:43])=[O:21])[C:12]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 186136627-Chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acidHCID 86589667Ethyl (trans)-4-(aminomethyl)-3-ethoxy-1-piperidinecarboxylate

Product 1

HCID 131723845(trans)-Ethyl 4-[[[(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)carbonyl]-amino]methyl]-3-ethoxy-1-piperidinecarboxylateYield 93.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

At a temperature below 10° C., triethylamine (0.01 mol) was added to 7-chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid (0.01 mol) in chloroform (40 ml). Ethyl chloroformate 01 mol) was added at a temperature below 10IC and the mixture was stirred for 30 minutes at a temperature below 10° C. This mixture was added to a solution of intermediate (14) (0.01 mol) in chloroform (20 ml), at a temperature below 10° C. The reaction mixture was stirred for 30 minutes then washed with a 5% HCl solution, with water, dried, filtered and the solvent was evaporated, yielding 4 g of (trans)-ethyl 4-[[[(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)carbonyl]-amino]methyl]-3-ethoxy-1-piperidinecarboxylate (intermediate 15).

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. washthen washed with a 5% HCl solution, with water
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9c0ebb7c8bd244aba26639c53ea16ce0
Source dataset
uspto-grants-2003_04
Patent number
US06544997B1

Reaction notes

Loading…