1,4-Dichlorobutane → 8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane chloride

HRID 1649473Notes

Reaction equation

HRID 1649473 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.[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17]Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl-: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 80591,4-DichlorobutaneHCID 10340Sodium CarbonateHCID 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 130541888-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane chlorideYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-pyrimidinyl)piperazine (32.8 g., 0.2 mole), 1,4-dichlorobutane (76.2 g., 0.6 mole) and finely powdered sodium carbonate (44.5 g., 0.42 mole) in 300 ml. of acetonitrile is stirred and refluxed for a 12-hour period. The hot reaction mixture is filtered and the filter cake washed with 50-100 ml.of hot acetonitrile. Combined filtrates are maintained at room temperature until crystallization occurs, then cooled, filtered, and collected material washed with acetone to provide a 70-90% yield of 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane chloride. This material is hygroscopic and after drying under vacuum at room temperature affords the monohydrate form melting about 90° C. which on continued drying under vacuum at 90° C. for several hours affords the anhydrous product having a melting point of about 210° C.

Workup

  1. temperaturerefluxed for a 12-hour period
  2. filtrationThe hot reaction mixture is filtered
  3. washthe filter cake washed with 50-100 ml
  4. temperaturecooled
  5. filtrationfiltered
  6. customcollected material
  7. washwashed with acetone

Sources & evidence

ORD record
ord-7b03672d50d24bb1902404fd71ada883
Source dataset
uspto-grants-1983_11
Patent number
US04417049

Reaction notes

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