1,3-Dichloropropane → HCID 12940907, compound

HRID 1863262Notes

Reaction equation

HRID 1863262 reaction equation
[CH2:1]([C:8]1[C:13]2[CH2:14][O:15][CH2:16][C:12]=2[C:11]([OH:17])=[C:10]([CH3:18])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][CH2:20][CH2:21][CH2:22][Cl:23].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:19][CH2:20][CH2:21][CH2:22][Cl:23].[Cl:19][CH2:20][CH2:21][CH2:22][O:17][C:11]1[C:12]2[CH2:16][O:15][CH2:14][C:13]=2[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[CH3:18]

Participants

7

Reactant 3

HCID 88811,3-DichloropropaneHCID 14798Sodium HydroxideHCID 129409064-Benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol

Product 2

HCID 88811,3-DichloropropaneHCID 12940907HCID 12940907, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 24.2 g (100 millimoles) of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol, 113 g (1 mole) of 1,3-dichloropropane, 2 g of benzyltriethylammonium chloride, 100 ml of toluene and 100 g of 50% strength sodium hydroxide solution is heated for 3 hours at 90° C., whilst stirring. The organic phase is separated off and washed with 50 ml of water. After stripping off the solvent and the excess 1,3-dichloropropane, 30.7 g of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-yl 3-chloropropyl ether are obtained; this material contains a small proportion of 1,3-bis-(4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-oxy)-propane which does not interfere with the subsequent reaction.

Workup

  1. customThe organic phase is separated off
  2. washwashed with 50 ml of water

Sources & evidence

ORD record
ord-9594aa4b05054a49b46cb62b3b5d0fcd
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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