Hydrochloric Acid → HCID 57656808, compound

HRID 2371183Notes

Reaction equation

HRID 2371183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][N:23]([CH2:25][CH3:26])[CH2:22][CH2:21][N:20]3C(OCC3C=CC=CC=3)=O)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][N:23]([CH2:25][CH3:26])[CH2:22][CH2:21][NH:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57656892HCID 57656892, compound

Product 1

HCID 57656808HCID 57656808, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To benzyl 2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]-4-ethylpiperazine-1-carboxylate (20 mg) was added 4M HCl in dioxane (1 ml). The solvent was evaporated, 1-methyl-2-pyrrolidinone (1 ml), zinc bromide (10 mg) and 10% palladium on carbon (50 mg) added and the mixture stirred under hydrogen at RT for 72 hours. Evaporation to dryness and purification on a 10 g SCX2 column, eluting sequentially with ethyl acetate, MeOH and 1% ammonia/MeOH gave the title compound (9 mg, 60%) by precipitation from CH2Cl2 with isohexane.

Workup

  1. customThe solvent was evaporated
  2. addition1-methyl-2-pyrrolidinone (1 ml), zinc bromide (10 mg) and 10% palladium on carbon (50 mg) added
  3. customEvaporation
  4. customto dryness and purification on a 10 g SCX2 column
  5. washeluting sequentially with ethyl acetate, MeOH and 1% ammonia/MeOH

Sources & evidence

ORD record
ord-4e3f6f2cef444747ad9e662f10eb28a6
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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