Ammonia → HCID 22660747, compound

HRID 1935688Notes

Reaction equation

HRID 1935688 reaction equation
C([N:8]1[C:16]2([CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:29])C1C=CC=CC=1.[Na].N.[Cl-:32].[NH4+]>CO>[ClH:32].[NH:19]1[CH2:20][CH2:21][C:16]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:29])[NH:8]2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 15548679HCID 15548679, compound

Product 1

HCID 22660747HCID 22660747, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Benzyl-1′-tert-butoxycarbonylspiro[1H-isoindole-1,4′-piperidine]-3(2H)-one (200 mg) was added to metallic sodium (235 mg) in liquid ammonia (10 mL) and the mixture was stirred for 30 minutes. To the reaction mixture was added methanol, neutralized with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue dissolved in methanol was stirred together with 4M hydrogen chloride/ethyl acetate at 50° C. for 1 hour. The reaction solution was concentrated to give the subject compound (591 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. dissolutionThe residue dissolved in methanol
  5. stirringwas stirred together with 4M hydrogen chloride/ethyl acetate at 50° C. for 1 hour
  6. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-4ade8c31dd054e75a59fda384d177dc7
Source dataset
uspto-grants-2002_05
Patent number
US06388077B1

Reaction notes

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