Sodium Hydroxide → 1-(2-Amino-1-ethyl)-4-(1,4-benzodioxan-5-yl)piperazine

HRID 369766

Reaction equation

HRID 369766 reaction equation
[Cl-].[Al+3].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-].[O:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]#[N:29])[CH2:23][CH2:22]3)[C:15]=2[O:14][CH2:13][CH2:12]1.[OH-].[Na+]>CCOCC.O1CCCC1.C(Cl)Cl>[NH2:29][CH2:28][CH2:27][N:24]1[CH2:23][CH2:22][N:21]([C:20]2[C:15]3[O:14][CH2:13][CH2:12][O:11][C:16]=3[CH:17]=[CH:18][CH:19]=2)[CH2:26][CH2:25]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 166981Aluminum;lithium;tetrachlorideHCID 6451240Aluminum(III) ChlorideHCID 10611289HCID 10611289, compound

Product 1

HCID 105876411-(2-Amino-1-ethyl)-4-(1,4-benzodioxan-5-yl)piperazineYield 95.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of lithium aluminium chloride (8.2 g) in dry ether (170 ml) was treated dropwise with a solution of aluminium chloride (8.2 g) in ether (170 ml) under cooling. After stirring for half an hour at room temperature a solution of 1-(1,4-benzodioxan-5-yl)-4-cyanomethylpiperazine (9.4 g) in dry tetrahydrofuran (250 ml) was added dropwise at 15° C. After reflux for 1.5 h the mixture was cooled and conc. sodium hydroxide solution (40 ml) was added dropwise. Filtration and removal of solvent in vacuo gave an oil which was dissolved in methylene chloride and dried over magnesium sulfate. Removal of solvent in vacuo gave 1-(2-amino-1-ethyl)-4-(1,4-benzodioxan-5-yl) piperazine (9.1 g) as a viscous oil.

Workup

  1. temperatureunder cooling
  2. additionwas added dropwise at 15° C
  3. temperatureAfter reflux for 1.5 h the mixture
  4. temperaturewas cooled
  5. filtrationFiltration and removal of solvent in vacuo
  6. customgave an oil which
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-2c8ab95ad6784dc889565f7a10dcfb75
Source dataset
uspto-grants-2000_10
Patent number
US06140331

Linked notes

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