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Hydrochloric Acid → (3R)-3-(3,4-dimethylbenzyl)-1-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine trihydrochloride

HRID 584204
Notes
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Reaction equation

HRID 584204 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]#[C:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][C:20]2([CH3:26])[CH3:25])[CH2:11][C@H:10]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=1)=O)(C)(C)C>C(OCC)(=O)C.C(O)C>[ClH:1].[ClH:1].[ClH:1].[CH3:35][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[CH3:34])[CH2:27][C@H:10]1[NH:9][CH2:14][CH2:13][N:12]([CH2:15][C:16]#[C:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][C:20]2([CH3:26])[CH3:25])[CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53964510(2R)-1-tert-butoxycarbonyl-2-(3,4-dimethylbenzyl)-4-[4-(3,3-dimethylmorpholino)-2-butynyl]-piperazine

Product 1

HCID 69677662(3R)-3-(3,4-dimethylbenzyl)-1-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine trihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

A solution of 4N hydrogen chloride in ethyl acetate was added to a solution of (2R)-1-tert-butoxycarbonyl-2-(3,4-dimethylbenzyl)-4-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine (40.0 g) in ethanol (120 ml) at room temperature and the whole was stirred for 12 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (500 ml) and potassium carbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (300 ml). The combined extract was dried over sodium sulfate and evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel using a mixed solvent of n-hexane and ethyl acetate (3:1). The fractions containing the objective compound were collected and evaporated under reduced pressure, and treated with 4N hydrogen chloride in ethyl acetate to give (3R)-3-(3,4-dimethylbenzyl)-1-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine trihydrochloride (37.7 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (500 ml) and potassium carbonate solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (300 ml)
  5. extractionThe combined extract
  6. dry with materialwas dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel using a mixed solvent of n-hexane and ethyl acetate (3:1)
  9. additionThe fractions containing the objective compound
  10. customwere collected
  11. customevaporated under reduced pressure
  12. additiontreated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-2c056dfc3df541f3a819893966c006fe
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06924278B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes