Butylamine → 6-(5-Cholesten-3beta-yloxy)hexylamine

HRID 851680Notes

Reaction equation

HRID 851680 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C@H:13]2[CH2:37][CH2:36][C@@:35]3([CH3:38])[C:15](=[CH:16][CH2:17][C@@H:18]4[C@@H:34]3[CH2:33][CH2:32][C@@:31]3([CH3:39])[C@H:19]4[CH2:20][CH2:21][C@@H:22]3[C@H:23]([CH3:30])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:14]2)C(=O)C2=CC=CC=C12.C(N)CCC>CO.C(Cl)(Cl)Cl>[CH3:29][CH:27]([CH2:26][CH2:25][CH2:24][C@H:23]([C@@H:22]1[C@:31]2([CH3:39])[C@H:19]([C@H:18]3[C@H:34]([CH2:33][CH2:32]2)[C@:35]2([CH3:38])[C:15]([CH2:14][C@@H:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH2:5])[CH2:37][CH2:36]2)=[CH:16][CH2:17]3)[CH2:20][CH2:21]1)[CH3:30])[CH3:28]

Participants

5

Reactant 2

HCID 8007ButylamineHCID 131790276-Phthalimido-1-(5-cholesten-3beta-yloxy)hexane

Product 1

HCID 131790296-(5-Cholesten-3beta-yloxy)hexylamineYield 43.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 6-phthalimido-1-(5-cholesten-3β-yloxy)hexane (500 mg) and n-butylamine (5 ml) in methanol (10 ml) and chloroform (5 ml) is heated under reflux for 1 hour. The solution is evaporated in vacuo to a residue that is put on a column of silica gel and eluted with CHCl3 -MeOH-NH4OH 90:10:1 (v/v/v). The ninhydrin positive fractions are combined and evaporated to give the title compound (170 mg, 43%).

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe solution is evaporated in vacuo to a residue that
  3. washeluted with CHCl3 -MeOH-NH4OH 90:10:1 (v/v/v)
  4. customevaporated

Sources & evidence

ORD record
ord-f348efed909c486d87f11d4cbc315a28
Source dataset
uspto-grants-1983_05
Patent number
US04386026

Reaction notes

Loading…