Diisopropylamine → HCID 22329453, compound

HRID 586415Notes

Reaction equation

HRID 586415 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:15]1[N:20]=[C:19]([N:21]2[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]2)[CH:18]=[C:17]([Cl:31])[N:16]=1.C(NC(C)C)(C)C>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[N:20]=[C:19]([N:21]3[CH2:30][CH2:29][C:24]4([O:25][CH2:26][CH2:27][O:28]4)[CH2:23][CH2:22]3)[CH:18]=[C:17]([Cl:31])[N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 759941-BenzylpiperazineHCID 22329430HCID 22329430, compound

Product 1

HCID 22329453HCID 22329453, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzylpiperazine (7.59 g, 43.1 mmol) was added to a solution of 8-(2,6-dichloro-4-pyrimidinyl)-1,4-dioxa-8-azaspiro[4.5]decane (10.0 g, 34.5 mmol) in tetrahydrofuran (100 mL), followed by diisopropylamine (9.26 g, 71.7 mmol). The reaction mixture was then heated at reflux overnight. The crude product was concentrated under reduced pressure and the residue was re-dissolved in CH2C12 and then washed with aqueous citric acid (2×100 mL) and brine (2×200 mL). The organic layer was dried over -anhydrous Na2SO4 and filtered. Upon standing, crystallization occurred, giving the desired product (12.4 g, 84%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux overnight
  3. concentrationThe crude product was concentrated under reduced pressure
  4. dissolutionthe residue was re-dissolved in CH2C12
  5. washwashed with aqueous citric acid (2×100 mL) and brine (2×200 mL)
  6. dry with materialThe organic layer was dried over -anhydrous Na2SO4
  7. filtrationfiltered
  8. customcrystallization

Sources & evidence

ORD record
ord-8e2a6c1868284ca2a6e95f43c4e4182f
Source dataset
uspto-grants-2005_08
Patent number
US06936607B2

Reaction notes

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