Sulfuric Acid → HCID 19760349, compound

HRID 1586974Notes

Reaction equation

HRID 1586974 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([CH2:11][C:12]3[CH:24]=[CH:23][C:15]([C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[O:4]CC1.S(=O)(=O)(O)O.[OH-].[Na+]>O1CCCC1.O>[CH2:21]([N:18]([CH2:19][CH3:20])[C:16](=[O:17])[C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[CH:24][CH:23]=1)[CH3:22]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19760357HCID 19760357, compound

Product 1

HCID 19760349HCID 19760349, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(1,4-Dioxa-8-azaspiro[4.5]dec-8-ylmethyl)-N,N-diethylbenzamide (63.9 g, 192 mmol) is dissolved in 193 mL of tetrahydrofuran and treated with a solution of concentrated sulfuric acid (77 mL) in water (309 mL). The solution is allowed to stir for three days and then refluxed for 17 hours. It is neutralized with 2.5N NaOH and extracted with 400 mL, 200 mL and then 100 of methylene chloride. The pooled extracts are dried over Na2SO4 and concentrated in vacuo affording 58.74 g (193 mmol, 100% yield) of product as a yellow oil: IR (thin film) 3500, 2980, 2810, 1720, 1630 cm-1 ; 1H NMR (Me2SO-d6, 400 MHz) δ7.4 (d,J=8.1 Hz, 2H), 7.3 (d,J=8.2 Hz, 2H), 3-3.6 (m, 8H), 2.68 (t,J=6.1 Hz, 2H), 2.34 (t,J= 6.0 Hz, 2H), 1.1 (m, 6H).

Workup

  1. temperaturerefluxed for 17 hours
  2. extractionextracted with 400 mL, 200 mL
  3. dry with materialThe pooled extracts are dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbb2fbcb17c04b7d9896734d92f00476
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

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