Diethyl (ethoxymethylene)malonate → HCID 21192583, compound

HRID 1068037Notes

Reaction equation

HRID 1068037 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C(O[CH:25]=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])C>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([N:8]([CH:25]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:9]2[CH:10]=[CH:11][C:12]([CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:13][CH:14]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonate2×HCID 21192601HCID 21192601, compound

Product 1

HCID 21192583HCID 21192583, compound

Conditions

Temperature
150 °C

Procedure

A flask containing 1-methyl-N-[4-(4morpholinylmethyl)phenyl]-4-piperidinamine (0.52 g) is treated with diethyl ethoxymethylenemalonate (0.55 mL). The flask is tightly capped and heated to 150° C. for 1 hour. The reaction is cooled to room temperature, treated with diethyl ethoxymethylenemalonate (0.55 mL) and heated to 180° C. for 2 hours. The reaction is cooled to room temperature and flash column chromatographed on silica eluting with 5% to 20% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.75 g of diethyl 2-{[(1-methyl-4-piperidinyl)-4-(4-morpholinylmethyl)anilino]methylene}malonate as tan solid.

Workup

  1. customThe flask is tightly capped
  2. temperatureThe reaction is cooled to room temperature
  3. temperatureheated to 180° C. for 2 hours
  4. temperatureThe reaction is cooled to room temperature
  5. customflash column chromatographed on silica eluting with 5% to 20% methanol in dichloromethane
  6. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-300d575579b64489b05ff502daa8f9a9
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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