1,4-Dibromobutane → 8-Aza-5-azoniaspiro(4.5)decane, 8-(2-pyrimidinyl)-, bromide (1:1)

HRID 905172

Reaction equation

HRID 905172 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[Br-:13].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N+:10]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 10340Sodium CarbonateHCID 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 6575058-Aza-5-azoniaspiro(4.5)decane, 8-(2-pyrimidinyl)-, bromide (1:1)Yield 84.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(2-pyrimidinyl)piperazine (32.8 g; 0.2 mole), 1,4-dibromobutane (108 g; 0.5 mole) and finely powdered sodium carbonate (21.2 g, 0.2 mole) in 400 mL isopropanol was stirred and refluxed for a 16 hr period. The hot reaction mixture was filtered and the filtrate, on standing at room temperature, provided 50.3 g (84% yield) of product. Crystallization of this material from isopropanol affords analytically pure product, m.p. 241.5°-242.5° C. (corr.).

Workup

  1. temperaturerefluxed for a 16 hr period
  2. filtrationThe hot reaction mixture was filtered
  3. customon standing at room temperature

Sources & evidence

ORD record
ord-0ede167535f74eb1b969017d63e15e53
Source dataset
uspto-grants-1983_12
Patent number
US04423049

Linked notes

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