Diethyl Ether → (2-{4-[Ethyl-(4-methoxy-benzenesulfonyl)-amino]-piperidin-1-yl}-ethyl)-carbamic acid tert-butyl ester

HRID 2354054Notes

Reaction equation

HRID 2354054 reaction equation
[CH2:1]([N:3]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[S:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29]Br)([CH3:24])([CH3:23])[CH3:22].CCN(C(C)C)C(C)C.CCOCC>C1COCC1>[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29][N:18]1[CH2:19][CH2:20][CH:15]([N:3]([CH2:1][CH3:2])[S:4]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:16][CH2:17]1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 58816568N-Ethyl-4-methoxy-N-piperidin-4-yl-benzenesulfonamide

Product 1

HCID 68690736(2-{4-[Ethyl-(4-methoxy-benzenesulfonyl)-amino]-piperidin-1-yl}-ethyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-ethyl-4-methoxy-N-piperidin-4-yl-benzenesulfonamide (Example A4., 1.19 g, 4 mmol), (2-bromo-ethyl)-carbamic acid tert-butyl ester (1.12 g, 5.0 mmol) and DIPEA (650 mg, 5 mmol) in THF (30 mL) is heated at reflux for 15 h. The solution is poured into Et2O (150 mL) and extracted with sat. aq. Na2CO3 (2×50 mL) and sat. aq. NaCl (30 mL), dried (Na2SO4), filtered and evaporated. The residue is purified by reversed phase MPLC to provide the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 15 h
  3. extractionextracted with sat. aq. Na2CO3 (2×50 mL) and sat. aq. NaCl (30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by reversed phase MPLC

Sources & evidence

ORD record
ord-7f11d70d9f3e46dba480a092bafe6930
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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