Acetic Acid → 1-(2-Methoxy-phenyl)4-(1,4-dioxa-spiro[4,5]dec-8-yl)-piperazine

HRID 428525Notes

Reaction equation

HRID 428525 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][N:23]([CH:7]2[CH2:8][CH2:9][C:4]3([O:11][CH2:1][CH2:2][O:3]3)[CH2:5][CH2:6]2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13461-(2-Methoxyphenyl)piperazineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 110020981-(2-Methoxy-phenyl)4-(1,4-dioxa-spiro[4,5]dec-8-yl)-piperazineYield 90.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1,4-cyclohexanedione monoethylene ketal (4.68 g, 30 mmol), 1-(2-methoxy-phenyl)piperazine (5.8 g, 30 mmol), sodium triacetoxyborohydride (9 g, 42 mmol) and acetic acid (1.8 ml, 30 mmol) in 1,2-dichloroethane (8 ml) was allowed to stir at room temperature for 12 hours. The reaction was quenched with 1N sodium hydroxide (pH>9), and extracted with methylene chloride (3×100 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. Chromatography (10% methanol-ethyl acetate) afforded 9.0 g (90%) of product as a semi-solid.

Workup

  1. customThe reaction was quenched with 1N sodium hydroxide (pH>9)
  2. extractionextracted with methylene chloride (3×100 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fa9f1394c32240a9b0209c33a028a8b4
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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