Chlorosuccinimide → HCID 68735147, compound

HRID 529113Notes

Reaction equation

HRID 529113 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][NH:23]C(OC(C)(C)C)=O)[N:15](C(OC(C)(C)C)=O)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:38]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:38])[C:20]=3[CH2:22][NH2:23])[NH:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68761759HCID 68761759, compound

Product 1

HCID 68735147HCID 68735147, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 1′-benzyl-4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,4′-piperidine]-1-carboxylate (115 mg, 0.227 mmol) in DCM (2 mL) was added 1-chloropyrrolidine-2,5-dione (NCS) (66 mg, 0.50 mmol). The reaction mixture was stirred at about room temperature for 48 hours. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was dissolved in DCM (2 mL) and treated with 4N HCl in dioxane (0.5 mL) overnight. The solvents were evaporated. The residue was taken up in DCM and basidified with saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM. The combined organic layers were washed with brine, dried and concentrated to give (1′-benzyl-5-chlorospiro[indoline-3,4′-piperidine]-4-yl)methanamine (40 mg, 52%) as an oil, which was used in the next step without further purification. LCMS (APCI+) m/z 342, 344 [M+H]+; Rt=1.71 min.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution and brine
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in DCM (2 mL)
  5. additiontreated with 4N HCl in dioxane (0.5 mL) overnight
  6. customThe solvents were evaporated
  7. extractionThe aqueous phase was extracted with DCM
  8. washThe combined organic layers were washed with brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-64958080d3e242e991a6ba0e1bc36c5a
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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