Formaldehyde → [1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 337211Notes

Reaction equation

HRID 337211 reaction equation
[CH2:1]=O.[C:3]([O:7][C:8](=[O:26])[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].C[O-].[Na+].[BH4-].[Na+]>CO.C(Cl)Cl>[C:3]([O:7][C:8](=[O:26])[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([NH:25][CH3:1])=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:14][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 43819146[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 71060136[1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 103.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Paraformaldehyde (0.15 g, 0.5 mmol) was added in one portion to pressure vessel containing [1-(4-amino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.12 g, 0.34 mmol) in Methanol (5 ml) at room temperature. To this mixture was added sodium methoxide (0.055 g, 1.02 mmol) in one portion, the pressure vessel was sealed and heated at 70° C. for 12 hours. After this time the reaction was cooled to room temperature and sodium borohydride (0.031 g, 0.82 mmol) added in one portion, the pressure vessel was re-sealed and heated at 70° C. for 1 hour. The reaction was then cooled to room temperature, diluted with DCM (20 ml) and washed with water (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.13 g, 99% yield) as a white solid which was taken on without further purification. Tr=1.96 min m/z (ES+) (M+Na+) 392.

Workup

  1. customthe pressure vessel was sealed
  2. temperatureAfter this time the reaction was cooled to room temperature
  3. customthe pressure vessel was re-sealed
  4. temperatureheated at 70° C. for 1 hour
  5. temperatureThe reaction was then cooled to room temperature
  6. washwashed with water (20 ml)
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c39ea2610a4d4cd9b5a4aca99ed3cdff
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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