Ammonia → HCID 19841741, compound

HRID 1638263Notes

Reaction equation

HRID 1638263 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[N:8]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:7]=[N:6][CH:5]=1.[CH3:17][N:18](C)C=[O:20].CN.N>ClC(Cl)Cl.CO>[OH2:20].[ClH:2].[ClH:1].[CH3:17][NH:18][CH2:3][C:4]1[N:8]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:7]=[N:6][CH:5]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 6329MethylamineHCID 18670818HCID 18670818, compound

Product 1

HCID 19841741HCID 19841741, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Through a stirred mixture of 3 parts of 5-(chloromethyl)-1-(1-phenylethyl)-1H-imidazole monohydrochloride and 45 parts of N,N-dimethylformamide were bubbled 3 equivalents of gaseous methanamine at room temperature during a 1 hour-period: exothermic reaction, the temperature rose to 50° C. The reaction mixture was taken up in trichloromethane and methanol, previously saturated with ammonia, was added. The formed precipitate was filtered off and the filtrate was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off, washed with 2-propanol, dried and crystallized from 2-propanol, yielding 1.6 parts (44.5%) of (±)-N-methyl-1-(1-phenylethyl)-1H-imidazole-5-methanamine dihydrochloride monohydrate; mp. 109° C. (compound 8.38).

Workup

  1. customexothermic reaction
  2. customrose to 50° C
  3. filtrationThe formed precipitate was filtered off
  4. customthe filtrate was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. filtrationThe salt was filtered off
  9. washwashed with 2-propanol
  10. customdried
  11. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-d43a5b82682742678f9f44c754a904b9
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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