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Methanol → 1-(4-Ethoxyphenyl)-4-[2-(isochroman-1-yl)ethyl]piperazine dihydrochloride hydrate

HRID 368841
Notes
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Reaction equation

HRID 368841 reaction equation
B.CSC.[CH:5]1([C:15](C)(C)[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][O:6]1.[ClH:35].O.CO>C1COCC1>[OH2:6].[ClH:35].[ClH:35].[CH2:31]([O:30][C:27]1[CH:26]=[CH:25][C:24]([N:21]2[CH2:22][CH2:23][N:18]([CH2:16][CH2:15][CH:5]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:8][CH2:7][O:6]3)[CH2:19][CH2:20]2)=[CH:29][CH:28]=1)[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 21885828Hydrate;hydrochlorideHCID 232888992-(Isochroman-1-yl)-1-[4-(4-ethoxyphenyl)piperazin-1-yl]-2-methylpropan-1-one

Product 1

HCID 232888801-(4-Ethoxyphenyl)-4-[2-(isochroman-1-yl)ethyl]piperazine dihydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide (0.8 ml, 0.08 mol) is added to a mixture of 2-(isochroman-1-yl)-1-[4-(4-ethoxyphenyl)piperazin-1-yl]-2-methylpropan-1-one (LXXXII, 0.279 g, 0.73 mmol) in THF (5 ml). The mixture is heated at 76° for 3 hr, then cooled in an ice/water bath. Hydrochloric acid/water (10%, 0.95 ml) is added, followed by methanol. The mixture is concentrated and additional methanol is added and removed under reduced pressure. This is repeated two more times. The residue is partitioned between dichloromethane and aqueous saturated sodium bicarbonate and the combined organic phases are separated and dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel eluting with methanol/dichloromethane (2/98). The appropriate fractions are pooled and concentrated to give the free base of the title compound. The dihydrochloride salt is prepared by dissolving the material in methanol and adding methanol saturated with hydrochloric acid to give the title compound, mp 211-212°; MS (m/z) 366; IR (mineral oil) 1510, 1117, 2329, 1257, 1475 and 2259 cm-1.

Workup

  1. temperatureThe mixture is heated at 76° for 3 hr
  2. temperaturecooled in an ice/water bath
  3. concentrationThe mixture is concentrated
  4. additionadditional methanol is added
  5. customremoved under reduced pressure
  6. customThe residue is partitioned between dichloromethane and aqueous saturated sodium bicarbonate
  7. customthe combined organic phases are separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue is chromatographed on silica gel eluting with methanol/dichloromethane (2/98)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2b2a573aafa24fbb90fe44e31bcd2caf
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06133446

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes