Ethyl formate → HCID 86751177, compound

HRID 1460100Notes

Reaction equation

HRID 1460100 reaction equation
[CH2:1]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([CH:11]([C:19]2[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=2)[C@@H:6]([CH3:32])[CH2:5]1)[CH:2]=[CH2:3].[CH:33](OCC)=[O:34]>>[CH2:1]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([CH:11]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([N:25]([CH2:26][CH3:27])[CH2:28][CH3:29])=[O:24])=[CH:30][CH:31]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH:33]=[O:34])[CH:13]=2)[C@@H:6]([CH3:32])[CH2:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 69941836HCID 69941836, compound

Product 1

HCID 86751177HCID 86751177, compoundYield 51%

Procedure

(±)-4-(α-(trans-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-aminobenzyl)-N,N-diethylbenzamide (0.42 g, 0.97 mmol) (Example 32, infra) was dissolved in 15 mL of ethyl formate and heated at reflux overnight under nitrogen. The reaction was concentrated to dryness and purified by chromatography on silica gel with ethanol (0-10%) in dichloromethane to give 0.23 g (51%) of (±)-trans-4-(α-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-formamidobenzyl)-N,N-diethylbenzamide. NMR (300 MHz, CDCl3): δ 1.0 (m, 3H) ; 1.2 (d, m, 9H); 1.8-2.2 (m, 3H); 2.4-2.9 (m, 5H); 3.2-3.6 (m, 5H); 5.1-5.3 (m, 3H) 5.8 (m, 1H); 6.7-7.8 (m, 8H); 7.9-8.1 (m, 1H), 8.6-8.9 (m, 1H). The amine was dissolved in ethanol and converted to the monohydrochloride salt by titration with ethanolic hydrogen chloride. The solution was concentrated to dryness. The resulting foam was dissolved in a minimal amount of ethanol and precipitated with diethyl ether to give 0.96 g of the hydrated monohydrochloride salt as an off-white solid. Calc. for C28H38N4O2HCl 1.5 H2O: C, 63.92; H, 8.05; N, 10.65; Cl, 6.74. Found: C, 64.21; H, 7.96; N, 10.77; Cl, 6.92.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight under nitrogen
  3. concentrationThe reaction was concentrated to dryness
  4. custompurified by chromatography on silica gel with ethanol (0-10%) in dichloromethane

Sources & evidence

ORD record
ord-8ca71855f6ca442ba1fca67dea586946
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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