Allylamine → HCID 10490871, compound

HRID 1720863Notes

Reaction equation

HRID 1720863 reaction equation
[CH2:1]([N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][C:7](N1CCC(NCC3C4C=CC=CC=4CCC4C=CC=CC3=4)CC1)=[N:8][C:9]=2[NH:13][CH2:14][CH:15]=[CH2:16])[CH:2]=[CH2:3].C(N)C=C.[Cl:44]C1N=C2C(N=CN2CC=C)=C(Cl)N=1>C(O)C>[Cl:44][C:7]1[N:6]=[C:5]2[C:10]([N:11]=[CH:12][N:4]2[CH2:1][CH:2]=[CH2:3])=[C:9]([NH:13][CH2:14][CH:15]=[CH2:16])[N:8]=1

Participants

5

Reactant 3

HCID 7853AllylamineHCID 9828017HCID 9828017, compoundHCID 10657004HCID 10657004, compound

Product 1

HCID 10490871HCID 10490871, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9-allyl-6-allylamino-2-{4-[(10,11-dihydro-5H-dibenzo-[a,d]cyclohepten-5-yl)methylamino]piperidino}purine ##STR14## 0.75 ml of allylamine is added to a solution of 1.15 g of 2,6-dichloro-9-allylpurine in 15 ml of ethanol and the mixture is stirred for 1 hour at room temperature and then heated at 50° C. for 30 minutes. After evaporation of the solvent, the mixture is taken up in CH2Cl2 -H2O, decanted, and the solvent is evaporated. The residue is recrystallised from ethanol. 1 g of 2-chloro-6-allylamino-9-allylpurine, melting at 110°-112° C. is obtained. 0.85 g of that compound is dissolved in 20 ml to butanol, 1.04 g of 4-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methylamino]-piperidine (oil), 0.5 g of K2CO3 and 0.1 g of potassium iodide are added to the solution obtained, and the mixture is heated at reflux for 10 hours. The reaction mixture is then concentrated and the residue is taken up in CH2Cl2 -H 2 O. The mixture is decanted, the organic phase is then evaporated, and the residue is chromatographed using ethyl acetate as eluant. 0.6 g of 9-allyl-6-allylamino-2-{4-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl) methylamino]piperidino}-purine is isolated in the form of crystals melting (cap) at 142°-144° C. The 9-allyl-2,6-dichloropurine used as starting material was prepared by reacting allyl alcohol and 2,6-dichloropurine in tetrahydrofuran according to the Mitsunobu method. The amine used as starting material was prepared by debenzylation of the corresponding piperidine melting at 78°-81° C., which was itself prepared by reductive alkylation with NaBH3CN, in methanol, of a mixture of 1-benzylpiperidone and (10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methylamine hydrochloride melting (cap) at 275°-280° C.

Workup

  1. temperatureheated at 50° C. for 30 minutes
  2. customAfter evaporation of the solvent
  3. customdecanted
  4. customthe solvent is evaporated
  5. customThe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-5438132e4cf24777b4a3fd2777a13a0f
Source dataset
uspto-grants-1996_04
Patent number
US05508277

Reaction notes

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