Triethylamine → HCID 18789400, compound

HRID 1106665Notes

Reaction equation

HRID 1106665 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[OH:24][CH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]1>C(Cl)Cl.C(Cl)(Cl)Cl>[OH:24][CH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 151442-Piperidin-2-ylethanolHCID 66986Myristoyl chloride

Product 1

HCID 18789400HCID 18789400, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.79 ml) and myristoyl chloride (1.270 g) were added to a solution of 2-(2-hydroxyethyl)piperidine (0.660 g) in methylene chloride (7 ml) under argon gas atmosphere while being cooled with ice. After being stirred for 2 hours, 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 50 g, chloroform:methanol=60:1), thereby yielding the entitled compound (1.664 g) as white solid.

Workup

  1. temperaturewhile being cooled with ice
  2. washwashed with 1N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=60:1)

Sources & evidence

ORD record
ord-55b269dcf6734fa4907fd9e2e7d0bc37
Source dataset
uspto-grants-2000_05
Patent number
US06057337

Reaction notes

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