Piperidine → HCID 67796802, compound

HRID 728661Notes

Reaction equation

HRID 728661 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:18])[N:3]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>C(O)C>[ClH:18].[ClH:18].[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]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 67796802HCID 67796802, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-(cis)-4-(2-amino-6-chloro-9H--purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (399 mg, 1.50 mmol) and piperidine (298 mg, 3.5 mmol) in absolute ethanol (10 mL) was refluxed under nitrogen for 1 hour. 1 N sodium hydroxide (1.5 mL) was added and the solution evaporated in dryness. The residue was chromatographed on silica gel. The title compound was eluted with 10% methanolchloroform as pale yellow glass (0.30 g). Precipitated as hydrochloride from acetonitrile; white powder (0.30 g, 52%); m.p. dec at 175-180° C.

Workup

  1. customthe solution evaporated in dryness
  2. customThe residue was chromatographed on silica gel
  3. washThe title compound was eluted with 10% methanolchloroform as pale yellow glass (0.30 g)
  4. customPrecipitated as hydrochloride from acetonitrile
  5. customm.p. dec at 175-180° C.

Sources & evidence

ORD record
ord-146957b6f3f6428b9fd5f7f17cf833ae
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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