Hydrochloric Acid → (S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloride

HRID 1609478Notes

Reaction equation

HRID 1609478 reaction equation
[ClH:1].[CH2:2]=O.Cl.Cl.[CH3:6][C:7]1[CH:8]=[C:9]([CH2:16][N:17]2[C:21]([CH2:22][C@@H:23]([C:25]([OH:27])=[O:26])[NH2:24])=[CH:20][N:19]=[CH:18]2)[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14]>>[ClH:1].[ClH:1].[CH3:6][C:7]1[CH:8]=[C:9]([CH2:16][N:17]2[C:21]3[CH2:22][C@@H:23]([C:25]([OH:27])=[O:26])[NH:24][CH2:2][C:20]=3[N:19]=[CH:18]2)[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 703463963-(3-methyl-4-nitrophenyl)methyl-L-histidine dihydrochloride

Product 1

HCID 70345643(S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochlorideYield 98%

Procedure

A 1N hydrochloric acid solution (13.7 ml) and a 37% formaldehyde solution (0.74 ml, 0.00907 mol) were added to 3-(3-methyl-4-nitrophenyl)methyl-L-histidine dihydrochloride (VIII-2) (1.1406 g, 0.00302 mol), and the mixture was stirred first at room temperature for half an hour and then on a 120° C. oil bath for 1.5 hours. The mixture was then cooled and concentrated to obtain the objective compound (VII-2) (1.1538 g; yield: 98.0%) as yellowish brown crystals (decomposed at 256.5°-258° C).

Workup

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated
  3. customto obtain the objective compound (VII-2) (1.1538 g; yield: 98.0%) as yellowish brown crystals (decomposed at 256.5°-258° C)

Sources & evidence

ORD record
ord-35fb4d7f4bb14ad5af9771b6eff05870
Source dataset
uspto-grants-1995_03
Patent number
US05401736

Reaction notes

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