1-(4-Nitrophenyl)pyrrolid-3-yl methanesulphonate → [3-(Imidazol-1-yl)propyl][1-(4-nitrophenyl)pyrrolid-3-yl]amine

HRID 719677Notes

Reaction equation

HRID 719677 reaction equation
CS(O[CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.NCCC[C:24]1[NH:25][CH:26]=[CH:27][N:28]=1>>[N:25]1([CH2:10][CH2:6][CH2:7][NH:8][CH:6]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[CH2:7]2)[CH:26]=[CH:27][N:28]=[CH:24]1

Participants

3

Reactant 2

HCID 120678141-(4-Nitrophenyl)pyrrolid-3-yl methanesulphonateHCID 132907973-(1H-Imidazol-2-yl)propan-1-amine

Product 1

HCID 58737022[3-(Imidazol-1-yl)propyl][1-(4-nitrophenyl)pyrrolid-3-yl]amineYield 48.2%

Procedure

30 g (0.105 mol) of 1-(4-nitrophenyl)pyrrolid-3-yl methylsulphonate (2) were heated at 90° C. for 18 hours with 120 g of aminopropylimidazole (0.958 mol). This mixture was poured into ice-cold water and the product was extracted with dichloromethane. The yellow powder obtained was chromatographed, eluting with dichloromethane/methanol (98/2), and 15.2 g of derivative (7) were recovered (48.2% yield).

Workup

  1. additionThis mixture was poured into ice-cold water
  2. extractionthe product was extracted with dichloromethane
  3. customThe yellow powder obtained
  4. customwas chromatographed
  5. washeluting with dichloromethane/methanol (98/2), and 15.2 g of derivative (7)
  6. customwere recovered (48.2% yield)

Sources & evidence

ORD record
ord-a22814a64c224890ada0c015d65c5f49
Source dataset
uspto-grants-2006_11
Patent number
US07132534B2

Reaction notes

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