Triethylamine → [6-[[(2-Piperidinoethyl)amino]carbonyl]-3-cyclohexenyl]methyl N-octadecylcarbamate

HRID 566427Notes

Reaction equation

HRID 566427 reaction equation
C(N(CC)CC)C.[CH2:8]([N:26]=[C:27]=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH:29][CH2:30][CH:31]1[CH:36]([C:37]([NH:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:38])[CH2:35][CH:34]=[CH:33][CH2:32]1>C(Cl)Cl>[CH2:8]([NH:26][C:27](=[O:28])[O:29][CH2:30][CH:31]1[CH:36]([C:37]([NH:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:38])[CH2:35][CH:34]=[CH:33][CH2:32]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 66988Octadecyl isocyanate2×HCID 212661176-(Hydroxymethyl)-N-(2-piperidinoethyl)-3-cyclohexene-1-carboxamide

Product 1

HCID 21266136[6-[[(2-Piperidinoethyl)amino]carbonyl]-3-cyclohexenyl]methyl N-octadecylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.96 ml) and octadecyl isocyanate (2.2 ml) were added to a solution of 6-(hydroxymethyl)-N-(2-piperidinoethyl)-3-cyclohexene-1-carboxamide (1.65 g) in methylene chloride (22 ml). After being stirred for 15 hours at room temperature, triethylamine (0.96 ml) and octadecyl isocyanate (2.2 ml) were further added to the reaction mixture and stirred for 5 hours at room temperature. The insoluble matters were filtrated out under a vacuum and washed with chloroform. The filtrate and washings were combined together and the mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=30:1-10:1), thereby yielding the entitled compound (2.59 g) as white solid.

Workup

  1. stirringstirred for 5 hours at room temperature
  2. filtrationThe insoluble matters were filtrated out under a vacuum
  3. washwashed with chloroform
  4. washthe mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  5. dry with materialdried over sodium sulfate anhydride
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=30:1-10:1)

Sources & evidence

ORD record
ord-2b59af2224d042a985fb4e7254dfe2ea
Source dataset
uspto-grants-2001_01
Patent number
US06174885B1

Reaction notes

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