Hydrochloric Acid → Spiro(indole-3,4'-piperidin)-2(1H)-one

HRID 565609Notes

Reaction equation

HRID 565609 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:22])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:22])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21268375tert-Butyl 2-oxo-1,2-dihydro-1'H-spiro[indole-3,4'-piperidine]-1'-carboxylate

Product 1

HCID 18435788Spiro(indole-3,4'-piperidin)-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1′-tert-butoxycarbonyl-spiro[3H-indole-3,4′-piperidin]-2(1H)-one, as described above in Step A, (551 mg, 1.70 mmol) in ethyl acetate saturated with HCl (5 mL) was stirred at ambient temp. for 3 hours as the product salt slowly crystallized out. This salt was collected by filtration and partitioned between methylene chloride and aqueous sat'd. sodium carbonate. The organic layer was separated off, dried (anhyd. sodium sulfate) filtered, and the solvent removed under vacuum. The residue was triturated with diethyl ether to give the title compound as a white solid, mp: 184-186° C.

Workup

  1. customslowly crystallized out
  2. filtrationThis salt was collected by filtration
  3. custompartitioned between methylene chloride and aqueous sat'd
  4. customThe organic layer was separated off
  5. dry with materialdried (anhyd. sodium sulfate)
  6. filtrationfiltered
  7. customthe solvent removed under vacuum
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-129bbeb1bee8434bab21c55ee132fbb2
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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