Triethylamine → HCID 135782141, compound

HRID 1905631Notes

Reaction equation

HRID 1905631 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.Cl.Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20]([NH2:26])([C:23](Cl)=[O:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N1CCC(N)(C(O)=O)CC1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[Na+]>C(Cl)Cl.C(Cl)CCl>[CH3:31][C:32]1[C:33]2[CH:28]=[CH:29][CH:30]=[CH:7][C:6]=2[NH:3][C:23](=[O:24])[C:20]2([CH2:21][CH2:22][N:17]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:18][CH2:19]2)[N:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 14803624-Amino-1-benzylpiperidine-4-carboxylic AcidHCID 88658736HCID 88658736, compound

Product 1

HCID 135782141HCID 135782141, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 12.2 g (0.12 mole) of triethylamine in 100 ml of methylene chloride is added dropwise to a mixture of 5.4 g (0.04 mole) of 2-aminocetophenone and 13.0 g (0.04 mole) of 1-benzyl-4-amino-4-piperidine-carboxylic acid chloride dihydrochloride (prepared from 9.4 g (0.04 mole) of 1-benzyl-4-amino-4-carboxypiperidine by reaction with excess phosphorus-V chloride in methylene chloride at 25° C.) in 400 ml of ethylene chloride at 0° C., while stirring and under an N2 atmosphere, and the mixture is stirred at 0° C. for 1 hour and finally at 25° C. for 2 hours. It is then poured onto ice, the pH is brought to 10 with sodium hydroxide solution and the reaction product is extracted with methylene chloride. For purification, the product is chromatographed on silica gel 60 (Merck), a methylene chloride/methanol mixture (10:1) being used as the eluting agent.

Workup

  1. stirringthe mixture is stirred at 0° C. for 1 hour and finally at 25° C. for 2 hours
  2. additionIt is then poured onto ice
  3. extractionthe reaction product is extracted with methylene chloride
  4. customFor purification
  5. customthe product is chromatographed on silica gel 60 (Merck)

Sources & evidence

ORD record
ord-d9f09585cac048b89ef6eed536373772
Source dataset
uspto-grants-1987_03
Patent number
US04647560

Reaction notes

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