Oxalic Acid → HCID 19429462, compound

HRID 1078372Notes

Reaction equation

HRID 1078372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.[BH4-].[Na+].[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25]>C(O)C.CCOCC>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:12][CH2:13][CH2:14][CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 226974'-ChloropropiophenoneHCID 787361H-Imidazole-1-propanamineHCID 4311764Sodium borohydride

Product 1

HCID 19429462HCID 19429462, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

In a similar manner to Example 1, a mixture of 4'-chloropropiophenone (8.4 g) and 1-(3-aminopropyl)imidazole (6.3 g) was heated at 120° C. for 9 hours. The cooled mixture was dissolved in absolute ethanol (100 ml), treated with sodium borohydride (3.9 g) and boiled under reflux for 16 hours. The oil obtained after work-up was dissolved in ether and treated with ethereal oxalic acid until the mixture was just acidic. The solid was filtered off and recrystallised from ethanol to give N-[1-(4-chlorophenyl)propyl]-3-(imidazol-1-yl)propylamine oxalate, m.p. 189°-190° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe oil obtained after work-up
  3. filtrationThe solid was filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4eea4ff1c7cd4bd8b3b46bfbd3fac5d9
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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