Dimethylformamide → 8-(2-Quinolinyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 580043Notes

Reaction equation

HRID 580043 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[O:12]1[C:16]2([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>O.CCOCC>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[N:19]1[CH2:20][CH2:21][C:16]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 141563948-(2-Quinolinyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g (0.0613) of 2-chloroquinoline, 27 g (0.1886 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 13 g (0.0941) of K2CO3, and 75 ml of dimethylformamide is stirred at 100°-110° C. for 4 days. The reaction mixture is allowed to cool to ambient temperature, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed copiously with water, then brine, dried over Na2SO4, and concentrated in vacuo to give a waxy solid. Trituration with ether furnishes 3.6 g (22%) of title compound: IR (KBr) 1620, 1610 and 1510 cm-1 ; NMR (CDCl3) δ7.92 (d, 1H), 7.78-7.50 (m, 3H), 7.30-7.22 (m, 1H), 7.04 (d, 1H), 4.02 (s, 4H), 3.94-3.86 (m, 4H), and 1.88-1.76 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed copiously with water
  3. dry with materialbrine, dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a waxy solid

Sources & evidence

ORD record
ord-210dd6efd9a54096b1be43afbd9069c0
Source dataset
uspto-grants-1988_06
Patent number
US04751305

Reaction notes

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