N,N-Dimethylethylenediamine → HCID 18442553, compound

HRID 458526Notes

Reaction equation

HRID 458526 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][C:11]=2[N:10]=[C:9]1[CH:18](Br)[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>CCO.CCOC(C)=O>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][C:11]=2[N:10]=[C:9]1[CH:18]([NH:26][CH2:25][CH2:24][N:23]([CH3:27])[CH3:22])[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 18442554HCID 18442554, compound

Product 1

HCID 18442553HCID 18442553, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3-benzyl-2-(1-bromopropyl)-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one (1-3, 0.080 g, 0.23 mmol) was dissolved in EtOH (2.0 mL) and treated with N,N-dimethyl ethylenediamine (0.05 mL, 0.46 mmol). The reaction was heated to 80° C. for 24 hours. The reaction was diluted with EtOAc (10 mL), washed with 5% NH4Cl, and dried over MgSO4. The organics were concentrated under reduced pressure to provide 3-benzyl-2-(1-{[2-(dimethylamino)-ethyl]amino}propyl)-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one (1-4). MS 355.1 found 354.5 required.

Workup

  1. washwashed with 5% NH4Cl
  2. dry with materialdried over MgSO4
  3. concentrationThe organics were concentrated under reduced pressure

Sources & evidence

ORD record
ord-e8b74345e1e1426583ac87e8d38f5ef5
Source dataset
uspto-grants-2007_03
Patent number
US07192949B2

Reaction notes

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