N,N-Dimethylethylenediamine → Benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylate

HRID 1256565Notes

Reaction equation

HRID 1256565 reaction equation
Cl[S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>C1COCC1>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH:25][S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 21931260Benzyl 4-(chlorosulfonyl)piperidine-1-carboxylate

Product 1

HCID 66698082Benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 430 mg (1.35 mmol) of benzyl 4-(chlorosulfonyl)-1-piperidinecarboxylate in 10 mL THF was treated with a 5-fold excess of N,N-dimethyl-ethylenediamine and the mixture was stirred at room temperature for 2 hrs. The THF was removed under vacuum. After dilution with water, the product was extracted with CH2Cl2 and dried. Chromatography on alumina, eluting with EtOAc, gave 450 mg (90% yield) of benzyl 4-({[2-(dimethylamino)ethyl]amino}sulfonyl)-1-piperidinecarboxylate as an oil: 1H NMR (CDCl3) δ 7.40-7.30 (m, 5H), 5.13 (s, 2H), 4.33 (m, exchangeable with D2O, 1H), 3.16 (m, 2H), 3.04 (tt, J=11.9, 3.7 Hz, 1H), 2.81 (br t, J=11.9 Hz, 1H), 2.43 (m, 2H), 2.22 (s, 6H), 2.12 (br d, J=12.8 Hz, 2H), 1.74 (ddd, J=25.0, 12.6, 4.5 Hz, 2H).

Workup

  1. customThe THF was removed under vacuum
  2. extractionAfter dilution with water, the product was extracted with CH2Cl2
  3. customdried
  4. washChromatography on alumina, eluting with EtOAc

Sources & evidence

ORD record
ord-6f61fc71428144f5a6bc2bd45eaf5557
Source dataset
uspto-grants-2013_06
Patent number
US08461158B2

Reaction notes

Loading…