Allyl bromide → Ethyl 4-(4-allyl-1,4-diazepan-1-yl)benzoate

HRID 1911456Notes

Reaction equation

HRID 1911456 reaction equation
Br[CH2:2][CH:3]=[CH2:4].[N:5]1([C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.CCN(C(C)C)C(C)C>ClCCl>[CH2:2]([N:8]1[CH2:9][CH2:10][CH2:11][N:5]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=2)[CH2:6][CH2:7]1)[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 18425301Ethyl 4-(1,4-diazepan-1-yl)benzoate

Product 1

HCID 66589947Ethyl 4-(4-allyl-1,4-diazepan-1-yl)benzoateYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromoprop-1-ene (0.433 mL, 5.00 mmol) was added to a stirred solution of ethyl 4-(1,4-diazepan-1-yl)benzoate (1.242 g, 5 mmol) and DIPEA (2.183 mL, 12.50 mmol) in dichloromethane (20 mL). The reaction mixture was stirred under nitrogen at room temperature for 24 h. This was diluted with dichloromethane (20 mL), washed with water (2×25 ml) and saturated sodium chloride solution (20 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% 2.5M ammonia/MeOH in DCM. Pure fractions were evaporated to dryness to afford ethyl 4-(4-allyl-1,4-diazepan-1-yl)benzoate (0.700 g, 48.5%) as a yellow oil.

Workup

  1. washwashed with water (2×25 ml) and saturated sodium chloride solution (20 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 5% 2.5M ammonia/MeOH in DCM
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-508423769de54726aa99bfca1fb05764
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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