Hydrochloric Acid → HCID 53759290, compound

HRID 1683050Notes

Reaction equation

HRID 1683050 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS(N=[C:29]=[O:30])(=O)=O.Cl.[OH-:32].[Na+]>ClCCl>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C:29](=[O:30])[NH:15][C:14]2=[O:32])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70918Chlorosulfonyl isocyanateHCID 30172221-Benzyl-4-((4-fluorophenyl)amino)piperidine-4-carbonitrile

Product 1

HCID 53759290HCID 53759290, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 1-benzyl-4-(4-fluoro-phenylamino)-piperidine-4-carbonitrile (32 mmol) and dichloromethane (100 mL). Add chlorosulfonyl isocyanate (20 mmol) in dropwise fashion with water bath cooling so as to maintain the temperature of the reaction mixture between 20° and 30° C. After 30 minutes, concentrate the reaction mixture in vacuo to obtain a residue. Add 1N HCl (100 mL) and heat at reflux for 1 h. Cool in an ice bath and adjust the pH to 5.5 using 5N NaOH. Filter to obtain a residue. Wash with diethyl ether and dry in vacuo. Purify to obtain the title compound.

Workup

  1. temperatureto maintain the temperature of the reaction mixture between 20° and 30° C
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto obtain a residue
  4. temperatureheat
  5. temperatureat reflux for 1 h
  6. temperatureCool in an ice bath
  7. filtrationFilter
  8. customto obtain a residue
  9. washWash with diethyl ether
  10. customdry in vacuo
  11. customPurify

Sources & evidence

ORD record
ord-338e9e40099c4d65af55b4c63fe06f8b
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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