Benzoic acid, 4-fluoro-, ethyl ester → Ethyl 4-(4-isopropyl-1,4-diazepan-1-yl)benzoate

HRID 1911461Notes

Reaction equation

HRID 1911461 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]([N:16]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14]>CS(C)=O.O>[CH:13]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:18][CH2:17]1)([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 122365131-(Propan-2-yl)-1,4-diazepane

Product 1

HCID 66589777Ethyl 4-(4-isopropyl-1,4-diazepan-1-yl)benzoateYield 36.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 4-fluorobenzoate (0.293 mL, 2 mmol) and 1-isopropyl-1,4-diazepane (0.539 mL, 4.00 mmol) in dimethylsulfoxide (10 mL), was heated at 120° C. for 18 h. The reaction mixture was diluted with water (75 ml) and extracted with ethyl acetate (3×25 ml). The extracts were washed with saturated sodium chloride solution (50 ml), dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford ethyl 4-(4-isopropyl-1,4-diazepan-1-yl)benzoate (0.212 g, 36.5%) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. washThe extracts were washed with saturated sodium chloride solution (50 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by silica column chromatography
  7. washeluting with a gradient of 0 to 5% MeOH in DCM
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-2cfbe9e060754dbc92bbd308d2e35596
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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