N-Benzylethylenediamine → HCID 19373577, compound

HRID 129190

Reaction equation

HRID 129190 reaction equation
Br[CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1.[CH2:16]([NH:23][CH2:24][CH2:25][NH2:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:12]([C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3][CH:2]([NH:26][CH2:25][CH2:24][NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]=2[CH:8]=1)#[N:13]

Participants

5

Reactant 3

HCID 77801N-BenzylethylenediamineHCID 516892Sodium BicarbonateHCID 102446284-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 19373577HCID 19373577, compoundYield 216.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (1.50 g, 5.64 mmole, from Example 8,part B) and N-benzylethylenediamine (8.48 g, 10 eq.) containing NaHCO3 (4.80 g, 5 eq.) in N,N-dimethylformamide (30 ml) was stirred for 48 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and distilled H2O. The organic phase was washed with distilled H2O, saturated NaCl solution, dried over Na2SO4 and evaporated in vacuo to obtain 4.10 g of an orange oil. The crude product was chromatographed on silica eluting with 9:1 methylene chloride/methanol (trace of NH4OH) to obtain 0.91 g (48%) of the title compound as a colorless gum. 1H NMR (CDCl3) δ8.00 (s, 1H), 7.49-7.34 (m, 6H), 6.88 (d, J=8.80 Hz, 1H), 3.93-3.82 (m, 3H), 3.03-2.80 (m, 5H), 2.25 (dd, J= 5.57 and 13.20 Hz, 1H), 1.67 (m, 1H), 1.53 (s, 3H), 1.35 (s, 3H); 13C NMR (CDCl3) δ157.66, 139.89, 132.52, 132.03,128.43, 128.14, 127.05, 125.55, 119.65, 118.06, 102.89, 76.86, 53.73, 49.38, 49.01, 45.32, 39.25, 36.40, 29.72, 25.02; MS: (M+H)+ @334.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. distillationdistilled H2O
  3. washThe organic phase was washed with distilled H2O, saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c32d432b872c430a84fda0ddcc852de9
Source dataset
uspto-grants-1995_11
Patent number
US05466817

Linked notes

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