Sulfamide → HCID 68924859, compound

HRID 2116751Notes

Reaction equation

HRID 2116751 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:22](N)([NH2:25])(=[O:24])=[O:23]>COCCOC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:22]([NH2:25])(=[O:24])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 15380687tert-Butyl 4-(benzylamino)piperidine-1-carboxylate

Product 1

HCID 68924859HCID 68924859, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2.05 g of 4-benzylamino-piperidine-1-carboxylic acid tert.-butyl ester and 3.39 g of sulfamide in 100 ml of 1,2-dimethoxy-ethane is refluxed for ca. 10 hours. From the mixture obtained solvent is evaporated, the evaporation residue obtained is treated with EtAc and unsoluble parts are filtered off. The filtrate obtained is subjected to chromatography on silica gel. 4-[N-(Aminosulfonyl)-benzylamino]-piperidine-1-carboxylic acid tert.butylester is obtained. mp 140-142°. 1H-NMR (DMSO) δ: 7.30-7.41 (s/m, 9+2H), 1.64 (m, 2H), 2.53-2.72 (broad, 2H), 3.71 (tt, 1H), 8.83-8.96 (broad, 2H), 4.26 (s, 2H, CH2), 6.86 (bs, 2H, NH), 7.19 (t, 1H), 7.28 (t, 1H), 7.36 (d, 1H). 13C-NMR (DMSO) δ:28.51, 30.13, 43.35, 47.11, 56.52, 79.12, 127.06, 127.48, 128.49, 140.59, 154.156.

Workup

  1. customFrom the mixture obtained solvent
  2. customis evaporated
  3. customthe evaporation residue obtained
  4. additionis treated with EtAc and unsoluble parts
  5. filtrationare filtered off
  6. customThe filtrate obtained

Sources & evidence

ORD record
ord-d43232646cae4b0c8fc770e6312df74d
Source dataset
uspto-grants-2008_10
Patent number
US07439362B2

Reaction notes

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