Sulfamide → HCID 19004203, compound

HRID 2225433Notes

Reaction equation

HRID 2225433 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[S:31](N)([NH2:34])(=[O:33])=[O:32]>O1CCOCC1>[C:17]1([CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:15][CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:31](=[O:33])(=[O:32])[NH2:34])=[CH:30][CH:29]=3)[CH2:13][CH2:12]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 19004206HCID 19004206, compound

Product 1

HCID 19004203HCID 19004203, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(4-aminophenethyl)-4-(diphenylmethoxymethyl)piperidine (200 mg, 0.50 mmol) (see Example 21) and sulphamide (480 mg, 5.0 mmol) in dioxane (5 ml) was heated under reflux for 3 hours and evaporated. The residue was partitioned between ethyl acetate and 10% aqueous potassium carbonate solution and the layers separated. The aqueous layer was extracted into ethyl acetate and the combined organic layers were dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-4% methanol as eluant. Appropriate fractions were combined and evaporated and the residue triturated with diisopropyl ether. The resulting solid was collected, washed with diisopropyl ether and dried to give the title compound (100 mg) as a pale yellow solid, m.p. 172°-174° C., which was characterised by its 1H-NMR spectrum.

Workup

  1. temperatureunder reflux for 3 hours
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and 10% aqueous potassium carbonate solution
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted into ethyl acetate
  6. dry with materialthe combined organic layers were dried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by chromatography on silica
  9. customevaporated
  10. customthe residue triturated with diisopropyl ether
  11. customThe resulting solid was collected
  12. washwashed with diisopropyl ether
  13. customdried

Sources & evidence

ORD record
ord-0fe991cb61d14827a1ea0e663580f094
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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