Hydrochloric Acid → 4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1095144Notes

Reaction equation

HRID 1095144 reaction equation
Cl[C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:42])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3C3C=C(Cl)C=CC=3OC3CCC4(OCCO4)CC3)[C:5]2=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>O1CCCC1.O>[Cl:22][C:18]1[CH:17]=[C:16]([CH:15]2[CH2:14][C:13](=[O:23])[NH:12][CH2:11][C:10]32[C:5]2[C:6](=[CH:7][CH:2]=[CH:3][CH:4]=2)[NH:8][C:9]3=[O:42])[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 866317946-chloro-2'-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 686290234'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.2 g, 0.32 mmol) in tetrahydrofuran (15 mL) and water (1 mL) was added aqueous HCl (2 N, 1 mL). The reaction mixture was stirred at room temperature for 1 h, then neutralized to “pH” 7 by aqueous NaHCO3 solution. The mixture was then extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:1) to give racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-cyclohexyloxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.1 g, 54%)

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:1)

Sources & evidence

ORD record
ord-2f3bd0262624468aa4962bf99ea2373b
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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