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Ammonium Chloride → 1'-(benzyl)-spiro[isobenzofuran-1(3H),4'-piperidin]-3-thione

HRID 1428506
Notes
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Reaction equation

HRID 1428506 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=O)[O:14]3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:32]2)=CC=1.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH2:7]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[S:32])[O:14]2)[CH2:10][CH2:9]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 87949Lawesson's reagentHCID 102664061'-Benzyl-3H-spiro[isobenzofuran-1,4'-piperidin]-3-one

Product 1

HCID 866679881'-(benzyl)-spiro[isobenzofuran-1(3H),4'-piperidin]-3-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 1′-(phenylmethyl)-spiro[isobenzofuran-1(3H),4′-piperidin]-3-one (25 g, 85.2 mmol) [C.A.S. 37663-42-6] in toluene (600 ml), was added 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (Lawesson's reagent) (34.47 g, 85.2 mmol was added. The reaction mixture was heated at 140° C. for 2 h. After cooling, the mixture was poured into NH4Cl (aqueous sat. solution) and extracted with DCM. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; DCM/MeOH 3% as eluent). The desired fractions were collected and concentrated in vacuo to a residue that was purified by HPLC to yield intermediate D72 (8 g, 30.3%).

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with DCM
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel; DCM/MeOH 3% as eluent)
  8. customThe desired fractions were collected
  9. concentrationconcentrated in vacuo to a residue that
  10. customwas purified by HPLC
  11. customto yield intermediate D72 (8 g, 30.3%)

Sources & evidence

ORD record
ord-2cc0fcef6b704a41bf89bbb681e37fd0
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937060B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes