Piperidine → HCID 22054167, compound

HRID 1830224Notes

Reaction equation

HRID 1830224 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.[CH3:19][O:20][C:21]1[C:22]([CH3:51])=[C:23]([C:42]([O:49][CH3:50])=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46])[CH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[C:27]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:26]=1>C(Cl)Cl>[CH3:19][O:20][C:21]1[C:22]([CH3:51])=[C:23]([C:42]([O:49][CH3:50])=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46])[CH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:30])=[C:27]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:26]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10275809HCID 10275809, compound

Product 1

HCID 22054167HCID 22054167, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperidine (56 mg, 0.6576 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (169 mg, 0.8815 mmol) were added to a methylene chloride solution (20 ml) of 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid (173 mg, 0.3827 mmol) and the resulting solution was stirred at room temperature for 8 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by flash column chromatography (hexand:ethyl acetate=2:1) to obtain the titled compound (129 mg, 0.2485 mmol, 65%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by flash column chromatography (hexand:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-502a6a09e764419487add428a8fa644e
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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