Nitrogen → 6-[4-(4-(5-Hydroxymethylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane

HRID 4961

Reaction equation

HRID 4961 reaction equation
C[O:2][C:3]([C:5]1[CH:33]=[CH:32][C:8]2[N:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:31]=[CH:30][C:25]5[O:26][CH2:27][CH2:28][O:29][C:24]=5[CH:23]=4)[CH2:18][CH2:17]3)[CH:10]=[N:11][C:7]=2[CH:6]=1)=O.N#N.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[OH:2][CH2:3][C:5]1[CH:33]=[CH:32][C:8]2[N:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:31]=[CH:30][C:25]5[O:26][CH2:27][CH2:28][O:29][C:24]=5[CH:23]=4)[CH2:20][CH2:21]3)[CH:10]=[N:11][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 197973276-[4-(4-(5-Methoxycarbonylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 197973286-[4-(4-(5-Hydroxymethylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.4 g of 6-[4-(4-(5-methoxycarbonylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane in 40 ml of THF is added dropwise with stirring in an N2 atmosphere at 20° to a suspension of 0.6 g of lithium aluminium hydride in 20 ml of THF. The mixture is stirred at 20° for 1 hour, decomposed with dilute sodium hydroxide solution and filtered, and the filtrate is worked up in the conventional manner and gives 6-[4-(4-(5-hydroxymethylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-22a8f936264443019aa427698e2e3d90
Source dataset
uspto-grants-1993_09
Patent number
US05242925

Linked notes

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