Triethylamine → HCID 19425237, compound

HRID 742422Notes

Reaction equation

HRID 742422 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[N:15]1[C:19](=[O:20])[C:18]2[CH2:21][CH2:22][CH2:23][CH2:24][C:17]=2[C:16]1=[O:25].[NH2:26][CH:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:29][CH2:28]1.C(N(CC)CC)C>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[CH:4][C:3]=1[NH:15][C:19](=[O:20])[C:18]1[CH2:21][CH2:22][CH2:23][CH2:24][C:17]=1[C:16]([NH:26][CH:27]1[CH2:28][CH2:29][N:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:31][CH2:32]1)=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 15279390N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 19425237HCID 19425237, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2-Fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (1.00 g, 2.75 mmol), ethyl 4-amino-1-piperidinecarboxylate (0.620 g, 3.60 mmol), triethylamine (0.310 g, 3.06 mmol) and benzene (25 ml) as a solvent were placed into a round bottom flask (50 cc) and stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting crude product was recrystallized from ether to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(1-ethoxycarbonyl-4-piperidyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.732 g, 50.9% yield).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting crude product was recrystallized from ether

Sources & evidence

ORD record
ord-100fb2ecad21443389d997724d0c4060
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

Loading…