Triethylamine → N-(1-Propylbutyl)-1,3-benzodioxole-5-carboxamide

HRID 339312Notes

Reaction equation

HRID 339312 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([NH2:8])[CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.[O:16]1[C:20]2[CH:21]=[CH:22][C:23]([C:25](Cl)=[O:26])=[CH:24][C:19]=2[O:18][CH2:17]1>ClCCl>[CH3:1][CH2:2][CH2:3][CH:4]([NH:8][C:25]([C:23]1[CH:22]=[CH:21][C:20]2[O:16][CH2:17][O:18][C:19]=2[CH:24]=1)=[O:26])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 386654-HeptanamineHCID 27347491,3-Benzodioxole-5-carbonyl chloride

Product 1

HCID 22831877N-(1-Propylbutyl)-1,3-benzodioxole-5-carboxamideYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of heptan-4-amine (8.06 mL, 54 mmol) in triethylamine (15.3 mL, 108 mmol) and dichloromethane (135 mL), was added, dropwise at 0° C., a solution of benzo[1,3]dioxole-5-carbonyl chloride (10 g, 54 mmol) dissolved in dichloromethane (135 mL). The reaction mixture was stirred for 1 h. Solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed successively with 1 N aq. HCl, 1 N aq. NaOH, water, brine, dried (MgSO4) and concentrated. The residue was recrystallized in EtOAc and Hexanes to afford 6.9 g of N-(heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide (48.3%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 0.92 (t, 6H), 1.38 (m, 6H), 1.53 (m, 2H), 4.11 (m, 1H), 5.63 (m, 1H), 6.01 (s, 2H), 7.98 (d, 1H), 7.27 (s, d, 2H). MS (M+H, 264).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was washed successively with 1 N aq. HCl, 1 N aq. NaOH, water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was recrystallized in EtOAc

Sources & evidence

ORD record
ord-7b2cd5fe250644b5adfc28ec78768bfb
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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