Benzylamine → HCID 59759974, compound

HRID 1693116Notes

Reaction equation

HRID 1693116 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:25][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 59759967HCID 59759967, compound

Product 1

HCID 59759974HCID 59759974, compound

Conditions

Temperature
160 °C

Procedure

A suspension of 4-(4-chloro-3-methanesulfonyl-phenyl)-pyridin (5.5 g) in benzylamine (23 ml) was heated to 160° C. for 4 h, concentrated under high vacuum. The residue was quenched with ice/water and extracted with ethyl acetate. The organic layers were washed, dried and concentrated; the residue was chromatographed on silica gel with heptane/ethyl acetate. The compound containing fractions were evaporated, and the residue crystallized from methanol/ether to obtain the desired compound (5.75 g) as an off-white solid. MS (ISP): 339.1 (M+H)+

Workup

  1. concentrationconcentrated under high vacuum
  2. customThe residue was quenched with ice/water
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was chromatographed on silica gel with heptane/ethyl acetate
  8. additionThe compound containing fractions
  9. customwere evaporated
  10. customthe residue crystallized from methanol/ether

Sources & evidence

ORD record
ord-39ef4abed84c42f59f2720fa44b0501b
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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