Triethylamine → HCID 53639650, compound

HRID 1106661Notes

Reaction equation

HRID 1106661 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][CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][NH:33]1>C(Cl)Cl.C(Cl)(Cl)Cl>[OH:29][CH2:30][CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][N:33]1[N:26]([CH2:8][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])[CH:27]=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 151442-Piperidin-2-ylethanolHCID 66988Octadecyl isocyanate

Product 1

HCID 53639650HCID 53639650, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (6.0 ml) and octadecyl isocyanate (11.500 g) were added to a solution of 2-(2-hydroxyethyl)piperidine (5.009 g) in methylene chloride (50 ml). After being stirred for 4 hours at room temperature, the reaction mixture was diluted with chloroform, washed with 1N hydrochloric acid, 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 200 g, chloroform:methanol=100:1~80:1), thereby yielding the entitled compound (15.662 g) as white solid.

Workup

  1. washwashed with 1N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (silica gel 200 g, chloroform:methanol=100:1~80:1)

Sources & evidence

ORD record
ord-9c2ea5c883d048569448fba6675242b2
Source dataset
uspto-grants-2000_05
Patent number
US06057337

Reaction notes

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