Meperidine hydrochloride → HCID 18957816, compound

HRID 2379036Notes

Reaction equation

HRID 2379036 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-0228692edfbb4338ad269f0ffc744012
Source dataset
uspto-grants-1994_11
Patent number
US05360805

Reaction notes

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