Thionyl Chloride → 5-[(4-Methyl-1-piperazinyl)-carbonyl]-8-chloro-1,4-benzodioxane

HRID 2286964Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.ClC1C2OCCOC=2C(C(Cl)=O)=CC=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>>[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([C:12]([C:5]2[C:6]3[O:11][CH2:10][CH2:9][O:8][C:7]=3[C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:14])[CH2:36][CH2:35]1

Participants

Reactant 4

HCID 24386Thionyl Chloride

HCID 531671-Methylpiperazine

HCID 205447468-Chloro-1,4-benzodioxane-5-carbonyl chloride

HCID 233670468-Chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid

Product 1

HCID 205447025-[(4-Methyl-1-piperazinyl)-carbonyl]-8-chloro-1,4-benzodioxaneYield 50.6%

Procedure

According to the method described in Example 33, 20 g of 8-chloro-1,4-benzodioxane-5-carboxylic acid were treated with thionyl chloride and the resulting 8-chloro-1,4-benzodioxane-5-carbonyl chloride (M.P.: 83° C.) was treated with 10.5 g of methylpiperazine. 14 g of 5-[(4-methyl-1-piperazinyl)-carbonyl]-8-chloro-1,4-benzodioxane were obtained (M.P.: 260° C. with decomposition; yield: 50.5%).

Sources & evidence

ORD record: ord-6e9d567f0d9a45228d0a8bd6b6a6dffd
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04268512

Reaction notes

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