Hydrochloric Acid → HCID 178525095, compound

HRID 1249103Notes

Reaction equation

HRID 1249103 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:23]([C:24]#[N:25])[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:26]=[N+:27]=[N-:28].[Na+].[NH4+].[Cl-].Cl>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH:23]([C:24]2[NH:28][N:27]=[N:26][N:25]=2)[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13863917HCID 13863917, compound

Product 1

HCID 178525095HCID 178525095, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3RS)-2-Benzyloxycarbonyl-3-cyano-1,2,3,4-tetrahydro-β-carboline (0.663 g), NaN3 (0.143 g), NH4Cl (0.118 g) and dimethylformamide (2 ml) is stirred at 95°-100° C. for 6 hours. The reaction mixture is cooled and then poured onto ice-water, adjusted to pH 2 with 10% HCl and extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried and distilled to remove the solvent. The residue is crystallized from ethyl acetate to give the title compound (0.358 g), m.p. 218°-219° C. (decomp.).

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto ice-water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. customdried
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-bf5fe3bd368b427db5cb6a6441348acc
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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