1-Benzyl-3-aminopyrrolidine → HCID 178527182, compound

HRID 1066175Notes

Reaction equation

HRID 1066175 reaction equation
Cl[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:5]=2[S:4](=[O:14])(=[O:13])[N:3]=1.[CH2:15]([N:22]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([N:22]1[CH2:26][CH2:25][CH:24]([NH:27][C:2]2[NH:7][C:6]3[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:5]=3[S:4](=[O:14])(=[O:13])[N:3]=2)[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 27566131-Benzyl-3-aminopyrrolidineHCID 127001053,7-dichloro-2H-1,2,4-benzothiadiazine 1,1-dioxide

Product 1

HCID 178527182HCID 178527182, compoundYield 72.9%

Conditions

Temperature
110 °C

Procedure

A suspension of 3,7-dichloro-4H-1,2,4-benzothiadiazine 1,1-dioxide (100 mg; 0.4 mmol) 1-benzyl-3-aminopyrrolidine (0.35 ml; 2.0 mmol) was stirred at 110° C. for 72 h. The reaction mixture was concentrated in vacu and the residue was purified by flash chromatography using ethyl acetate/methanol 10:1 to give oily crystals (114 mg). These were recrystallised from ethyl acetate to give the title compound as white crystals (83 mg, 53%); m.p. 208.5-209.5° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacu
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6581da008e074db99c7f731722ad735c
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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