Hydrochloric Acid → HCID 57656634, compound

HRID 2371166Notes

Reaction equation

HRID 2371166 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][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH:27]4[CH2:32][CH2:31][N:30](C(OCC5C=CC=CC=5)=O)[CH2:29][CH2:28]4)[CH2:20]3)[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][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57656639HCID 57656639, compound

Product 1

HCID 57656634HCID 57656634, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To benzyl 4-(2-{(3R)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidin-1-yl}ethyl)piperidine-1-carboxylate (805 mg) was added 4M HCl in dioxane (5 ml). After removal of the solvent, 1-methyl-2-pyrrolidinone (5 ml) and zinc bromide (20 mg) were added, the mixture purged with Argon, 10% Pd/C (100 mg) added and stirred under hydrogen for 60 hours. Catalyst was filtered off through Celite, fresh catalyst and zinc bromide added and stirring continued for a further 48 hours under hydrogen. After filtration, the mixture was purified on a SCX2.50 g column, eluting sequentially with isohexane, ethyl acetate, 50% ethyl acetate/MeOH, MeOH and finally with 10% ammonia in MeOH to give the title compound (205 mg, 34%).

Workup

  1. customAfter removal of the solvent, 1-methyl-2-pyrrolidinone (5 ml) and zinc bromide (20 mg)
  2. additionwere added
  3. customthe mixture purged with Argon, 10% Pd/C (100 mg)
  4. additionadded
  5. filtrationCatalyst was filtered off through Celite, fresh catalyst and zinc bromide
  6. additionadded
  7. stirringstirring
  8. waitcontinued for a further 48 hours under hydrogen
  9. filtrationAfter filtration
  10. customthe mixture was purified on a SCX2
  11. wash50 g column, eluting sequentially with isohexane, ethyl acetate, 50% ethyl acetate/MeOH, MeOH and finally with 10% ammonia in MeOH

Sources & evidence

ORD record
ord-9903cce4a44e45918d349a94d86fb2e3
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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