Diisopropyl Ether → HCID 68888497, compound

HRID 857908Notes

Reaction equation

HRID 857908 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([NH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)(=[O:10])[CH3:9].C(OC(C)C)(C)C>C(O)=O>[CH3:16][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[C:19]([CH2:1][N:2]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)[CH:18]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 531671-MethylpiperazineHCID 739424-Acetamidobenzaldehyde

Product 1

HCID 68888497HCID 68888497, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
-10 °C

Procedure

A stirred solution of formic acid (3.77 mL) at −10° C. was treated with 1-methylpiperazine (11.10 mL) dropwise whilst maintaining the temperature at −10° C. The reaction mixture was then allowed to warm to room temperature and treated with 4-acetamidobenzaldehyde (4.08 g). After stirring at 130° C. for 15 minutes the temperature was increased to 155° C. and stirring continued for 2.5 hours. The reaction mixture was allowed to cool to room temperature and treated with diisopropyl ether (50 mL). The insoluble material was washed with diethyl ether to give the title compound (3.98 g) as buff crystalline solid, m.p. 106–108° C. MS: 248 [MH]+.

Workup

  1. temperatureto warm to room temperature
  2. temperaturewas increased to 155° C.
  3. stirringstirring
  4. waitcontinued for 2.5 hours
  5. temperatureto cool to room temperature
  6. washThe insoluble material was washed with diethyl ether

Sources & evidence

ORD record
ord-337d54bd2b1c4e1c9ab241f0bc50e0b6
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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