Ethyl piperidine-2-carboxylate → HCID 15125474, compound

HRID 2106757Notes

Reaction equation

HRID 2106757 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])OC4C=CC=CC=4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1[C:37](OCC)=[O:38].O1CCOCC1>CN(C)C1C=CN=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:16]=[CH:17][C:18]([N:21]4[C:37](=[O:38])[CH:32]5[CH2:33][CH2:34][CH2:35][CH2:36][N:31]5[C:22]4=[O:30])=[CH:19][CH:20]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 27517Ethyl piperidine-2-carboxylateHCID 312751,4-DioxaneHCID 981607Phenyl N-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate

Product 1

HCID 15125474HCID 15125474, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 50 parts of phenyl [4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]carbamate, 22.7 parts of ethyl 2-piperidinecarboxylate, 4 parts of N,N-dimethyl-4-pyridinamine and 300 parts of 1,4-dioxane was stirred for 5 hours at reflux temperature. After saturation with water, the reaction mixture was heated for 30 minutes. After cooling, the precipitated product was filtered off, washed with 2-propanol and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1-butanol. The product was filtered off and dried, yielding 24.8 parts (47.5%) of 5,6,7,8-tetrahydro-2-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]imidazo[1,5-a]pyridine-1,3(2H,8aH)-dione; mp. 223.4° C. (int. 17).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe precipitated product was filtered off
  4. washwashed with 2-propanol
  5. custompurified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 1-butanol
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-f14e97475c584bc6bc2c61d7a54933be
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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