Hydrochloric Acid → HCID 20225061, compound

HRID 1249183Notes

Reaction equation

HRID 1249183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=3)[NH:14][C:15](=O)[CH2:16][O:17][CH3:18])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.O>O1CCCC1.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=3)[NH:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 20225049HCID 20225049, compound

Product 2

HCID 313Hydrochloric AcidHCID 20225061HCID 20225061, compoundYield 41,703.699%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulphide complex (5 ml) was added dropwise to a solution of the acetamide (3.3 g) prepared as above in tetrahydrofuran (100 ml) and the mixture stirred for 2 days. Ice-water was added cautiously and the resulting mixture basified. The basified mixture was extracted with ether and the extracts washed and dried. Removal of the ether gave a residue which was dissolved in ether. Hydrogen chloride gas was passed through the solution to give a hydrochloride of N-{[1-(3,4-dichlorophenyl)cyclobutyl][1-methylimidazol-2-yl]methyl}-2-methoxyethylamine containing 1.8 moles of hydrochloride and 1.6 moles of water which decomposed when heated to 150° C.

Workup

  1. extractionThe basified mixture was extracted with ether
  2. washthe extracts washed
  3. customdried
  4. customRemoval of the ether
  5. customgave a residue which

Sources & evidence

ORD record
ord-3d949d243d5e42af9342b09baaf1cbe0
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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