Palmitoyl chloride → HCID 178443118, compound

HRID 19748

Reaction equation

HRID 19748 reaction equation
[OH:1][CH:2]([CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:3][O:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[NH:7].C(N(CC)CC)C.[C:28]([Cl:45])(=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>C(Cl)(Cl)Cl>[ClH:45].[C:28]([O:1][CH:2]([CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:3][O:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[NH:7])(=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 8206Palmitoyl chloride2×HCID 8471Triethylamine2×HCID 178513416HCID 178513416, compound

Product 1

HCID 178443118HCID 178443118, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

14.7 g (52.8 mmol) of N-[2-hydroxy-3-(1-piperidinyl)propoxy]-3-pyridine-carboximidamide [Hung. Pat. 177.578 (1976)] was dissolved in 160 ml of chloroform. 7.7 ml (55 mmol) of triethylamine was added, followed by dropwise addition of a solution of palmitoyl chloride (14.7 g; 56.5 mmol) in 85 ml of chloroform. The mixture was stirred overnight at room temperature. Next day further amount of 3.8 ml of triethylamine and 7.4 g of palmitoylchloride was added, and the stirring was continued for one more day. The solution was extracted then with water, 5% acetic acid and water, successively, dried over anh. sodium sulfate, and evaporated to dryness.

Workup

  1. extractionThe solution was extracted
  2. dry with materialwith water, 5% acetic acid and water, successively, dried over anh. sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-580966e9b0a742c6aecadfce7399d1a3
Source dataset
uspto-grants-2010_06
Patent number
US07745465B2

Linked notes

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