Meperidine hydrochloride → HCID 18957816, compound

HRID 483798Notes

Reaction equation

HRID 483798 reaction equation
CCO[C:4]([C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)=[O:5].Cl.[CH2:20]([NH2:24])[CH2:21][CH2:22][CH3:23].[OH-].[Na+]>C(OCC)C>[CH2:20]([NH:24][C:4]([C:6]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH2:8][N:9]([CH3:12])[CH2:10][CH2:11]1)=[O:5])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 5750Meperidine hydrochlorideHCID 8007ButylamineHCID 14798Sodium Hydroxide

Product 1

HCID 18957816HCID 18957816, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pethidine hydrochloride (2.56 g, 9 mmol) and butylamine (5 ml) were heated in an autoclave at 180° C. for 3 days. The reaction mixture was shaken between 10 ml of 1N NaOH and diethyl ether and the ether extracts dried (MgSO4). The solvent was evaporated and the residue chromatographed on aluminium oxide with ethyl acetate as eluent. The crystalline product (1.0 g) was recrystallized from n-hexane yielding 0.59 g with m.p. 73°-76.5° C.

Workup

  1. dry with materialthe ether extracts dried (MgSO4)
  2. customThe solvent was evaporated
  3. customthe residue chromatographed on aluminium oxide with ethyl acetate as eluent
  4. customThe crystalline product (1.0 g) was recrystallized from n-hexane yielding 0.59 g with m.p. 73°-76.5° C.

Sources & evidence

ORD record
ord-a7cf420fa8b541f19c4776eab999b597
Source dataset
uspto-grants-1993_07
Patent number
US05227389

Reaction notes

Loading…