Dimethylformamide → HCID 20357451, compound

HRID 2083722Notes

Reaction equation

HRID 2083722 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[O:22]([CH2:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38]Cl)[CH2:32][CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:38][CH2:37][CH2:36][N:33]1[CH2:32][CH2:31][CH:30]([CH2:29][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 53592776-ChloropurineHCID 20570886HCID 20570886, compound

Product 1

HCID 20357451HCID 20357451, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 15.4 g (0.1 mole) of 6-chloropurine, 75 ml of N,N-dimethyl formamide, 13.8 g (0.1 mole) of potassium carbonate and 26.8 g (0.1 mole) of 3-(4-phenoxymethylpiperidino)-propyl chloride is heated to 40° C for 6 hours, while stirring. The reaction mixture is then mixed with water extracted with ethyl acetate and the extract is dried and evaporated. The residue obtained is recrystallized from ethyl acetate/ligroin. There are obtained 16.2 g (42% of theory) of 6-chloro-9-[3-(4-phenoxymethylpiperidino)-propyl]-purine; m.p. 95° - 96° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe extract is dried
  3. customevaporated
  4. customThe residue obtained
  5. customis recrystallized from ethyl acetate/ligroin

Sources & evidence

ORD record
ord-68178bf4cadb43d9bccd2e6e79a17dc3
Source dataset
uspto-grants-1978_04
Patent number
US04086347

Reaction notes

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