Hydrochloric Acid → HCID 70076743, compound

HRID 1291826Notes

Reaction equation

HRID 1291826 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][N:14]([CH3:16])C)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:21][O:22][C:23]1[CH:28]=C[CH:26]=[C:25](N)[CH:24]=1.Cl>C(O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][NH:14][C:16]2[CH:26]=[CH:25][CH:24]=[C:23]([O:22][CH3:21])[CH:28]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108243-MethoxyanilineHCID 54308355HCID 54308355, compound

Product 1

HCID 70076743HCID 70076743, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product of step (ii) (6.3 g), m-anisidine (2.5 ml), ethanol (65 ml) and concentrated hydrochloric acid (2.2 ml) was stirred at room temperature for 2 hours then evaporated. The residue was basified by careful addition of aqueous sodium carbonate solution. The mixture was extracted with ethyl acetate and the organic extracts were washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by flash chromatography on silica by elution with 70% v/v ether/hexane to yield 1-ethoxycarbonyl-4-(1-(3-methoxyphenyl)amino-2-methoxycarbonylethen-2-yl)piperazine (5.15 g) as an off-white solid: m.p. 120°-122° C.; NMR (CDCl3) δ 1.28 (3H, t), 2.90 (4H, m), 3.50 (4H, m), 3.71 (3H, s), 3.81 (3H, s), 4.18 (2H, q), 6.52 (3H, m), 7.21 (1H, t), 7.39 (1H, d), 7.80 (1H, d); m/Z 364 (H+H)+.

Workup

  1. customthen evaporated
  2. additionThe residue was basified by careful addition of aqueous sodium carbonate solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica by elution with 70% v/v ether/hexane

Sources & evidence

ORD record
ord-cd23bbca47394d93901b8904da0c817e
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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