1-Iodopropane → Diethyl 4-(ethylpropylamino)benzylacetamidomalonate

HRID 1934317Notes

Reaction equation

HRID 1934317 reaction equation
[CH2:1]([NH:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][CH2:9][C:10]([NH:12][CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11])=[CH:6][CH:5]=1)[CH3:2].I[CH2:27][CH2:28][CH3:29].N12CCCC1=NCCC2>O1CCCC1>[CH2:1]([N:3]([CH2:27][CH2:28][CH3:29])[C:4]1[CH:25]=[CH:24][C:7]([CH2:8][CH2:9][C:10]([NH:12][CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 54294942Diethyl 4-ethylaminobenzylacetamidomalonate

Product 1

HCID 53944907Diethyl 4-(ethylpropylamino)benzylacetamidomalonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Working as in Example F, but starting with 10 g of diethyl 4-ethylaminobenzylacetamidomalonate, 5.6 ml of 1-iodopropane and 7.2 ml of 1,5-diazabicyclo-[4.3.0] non-5-ene in 70 ml of tetrahydrofuran, and after reacting for 36 hours followed by purification by flash chromatography (eluent: 97/3 CH2Cl2/MeOH by volume), 2.8 g of a solid are obtained, which solid is recrystallized from 26 ml of cyclohexane. 2.9 g of diethyl 4-(ethylpropylamino)benzylacetamidomalonate are thus obtained in the form of a white solid melting at 84-86° C.

Workup

  1. customfollowed by purification by flash chromatography (eluent: 97/3 CH2Cl2/MeOH by volume), 2.8 g of a solid
  2. customare obtained
  3. customwhich solid is recrystallized from 26 ml of cyclohexane

Sources & evidence

ORD record
ord-4f8b4f3358784c939681f362f1a181e5
Source dataset
uspto-grants-2002_05
Patent number
US06384014B1

Reaction notes

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