HCID 12109168, compound → HCID 18392475, compound

HRID 1274180Notes

Reaction equation

HRID 1274180 reaction equation
[BrH:1].C(O)(=O)C.[N:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:34])[C:14]2[CH:19]=[CH:18][C:17]([C@H:20]([NH:22]C(OCC3C=CC=CC=3)=O)[CH3:21])=[C:16]([Cl:33])[CH:15]=2)=[CH:8][CH:7]=1>>[BrH:1].[BrH:1].[N:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:34])[C:14]2[CH:19]=[CH:18][C:17]([C@H:20]([NH2:22])[CH3:21])=[C:16]([Cl:33])[CH:15]=2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 12109168HCID 12109168, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 18392475HCID 18392475, compound

Procedure

A 25% hydrogen bromide-acetic acid solution (7 ml) was added to (R)-N-(4-pyridyl)-4-(1benzyloxycarbonylaminoethyl)-3-chlorobenzamide (630 mg), and the mixture was stirred at room temperature for 6 hours. After the reaction, the solvent was evaporated under reduced pressure. The obtained crystals were washed with ether, and recrystallized from methanol to give 243 mg of (R)-(+)-N-(4-pyridyl)-4-(1aminoethyl)-3-chlorobenzamide dihydrobromide having a melting point of more than 300° C.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. washThe obtained crystals were washed with ether
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2c82be2ff61945f0852f83c37053fea2
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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