Hydrochloric Acid → Oleic acid-2-{[3-(4-amino-piperidin-1-yl)-propyl]-(2-oleoyloxy-ethyl)-amino}-ethyl ester

HRID 11192

Reaction equation

HRID 11192 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:14][OH:15])[CH2:5][CH2:4]1.C(N([CH:25]([CH3:27])[CH3:26])C(C)C)C.C(OC(OC(O[C:39]([CH3:42])([CH3:41])C)=O)=O)(C)(C)C.[C:43](Cl)(=[O:61])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60].Cl>ClCCl>[NH2:2][CH:3]1[CH2:4][CH2:5][N:6]([CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][O:18][C:43](=[O:61])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53][CH2:54][CH2:42][CH2:39][CH2:41][CH2:27][CH2:25][CH3:26])[CH2:13][CH2:14][O:15][C:43](=[O:61])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[CH2:7][CH2:8]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 5364783Oleoyl chlorideHCID 219672332-{[3-(4-Amino-piperidin-1-yl)-propyl]-(2-hydroxy-ethyl)-amino}-ethanol-hydrochloride

Product 1

HCID 86590578Oleic acid-2-{[3-(4-amino-piperidin-1-yl)-propyl]-(2-oleoyloxy-ethyl)-amino}-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4.5 g (4 mmol) of the 2-{[3-(4-amino-piperidin-1-yl)-propyl]-(2-hydroxy-ethyl)-amino}-ethanol-hydrochloride described in example 10 in 100 ml dichloromethane is admixed with 3.5 g N-ethyl-diisopropylamine and 0.87 g (4 mmol) pyrocarbonic acid di-t-butyl ester, it is refluxed for 18 h, a solution of 2.4 g (8 mmol) oleoyl chloride in 40 ml dichloromethane is added dropwise, it is refluxed for 18 h, admixed with 15 ml etheric hydrogen chloride solution and stirred for 6 h at room temperature. It is concentrated by evaporation, adjusted to pH 9 with N sodium hydroxide solution, extracted with dichloromethane and methanol, dried and concentrated by evaporation. After chromatography on silica gel (eluting agent ethyl acetate/methanol 1:1) 1.1 g (36% of theory) of the title compound is isolated as an oil.

Workup

  1. temperatureis refluxed for 18 h
  2. temperatureit is refluxed for 18 h
  3. concentrationIt is concentrated by evaporation
  4. extractionextracted with dichloromethane and methanol
  5. customdried
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7afa7b65fe894f658bd2a222ed482b09
Source dataset
uspto-grants-2006_08
Patent number
US07097854B2

Linked notes

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