1,8-Octanediamine → HCID 67588122, compound

HRID 728662Notes

Reaction equation

HRID 728662 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28])[N:3]=1

Participants

4

Reactant 2

HCID 242501,8-OctanediamineHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 67588122HCID 67588122, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-(cis)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (272 mg, 1.00 mmol) and 1,8-diaminooctane (1.44 g, 10 mmol) in absolute ethanol (15 mL) was refluxed under nitrogen for 1.5 hours. The solution was concentrated, cooled, and the resulting precipitate filtered and crystallised from i-propanol to give title compound as white solid (160 mg, 42%), m.p. 125-127° C.

Workup

  1. concentrationThe solution was concentrated
  2. temperaturecooled
  3. filtrationthe resulting precipitate filtered
  4. customcrystallised from i-propanol

Sources & evidence

ORD record
ord-5077077f16954aab92707dab9f5bec89
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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