Formaldehyde → 4-Hydroxy-5-(4-propylpiperazinylmethyl)-1,3-benzodioxole

HRID 1198391Notes

Reaction equation

HRID 1198391 reaction equation
[CH2:1]=O.[OH:3][C:4]1[C:12]2[O:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH2:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:14][CH3:15]>C(#N)C>[OH:3][C:4]1[C:12]2[O:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][C:5]=1[CH2:1][N:19]1[CH2:20][CH2:21][N:16]([CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 415812Piperazine, 1-propyl-, hydrochloride (1:2)HCID 5867271,3-Benzodioxol-4-ol

Product 1

HCID 191026294-Hydroxy-5-(4-propylpiperazinylmethyl)-1,3-benzodioxoleYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Aqueous formaldehyde (37%; 3.67 g, 45.3 mmol) was added dropwise to a stirred solution of 4-hydroxy-1,3-benzodioxole (5.2 g, 37.8 mmol) and N-propylpiperazine (5.8 g, 45.3 mmol) in acetonitrile (25 ml). The reaction mixture was stirred at room temperature for one hour and evaporated in vacuo. The remaining oil (13.0 g) was purified chromatographically (with ethylacetate/methanol=9/1 (v/v) as an eluent to give 4-hydroxy-5-(4-propylpiperazinylmethyl)-1,3-benzodioxole (5.9 g, 56% yield; compound No. 25), m.p. 115°-117° C.

Workup

  1. customevaporated in vacuo
  2. customThe remaining oil (13.0 g) was purified chromatographically (with ethylacetate/methanol=9/1 (v/v) as an eluent

Sources & evidence

ORD record
ord-4d9fd957af3f430d94019af0df79654a
Source dataset
uspto-grants-1994_01
Patent number
US05281595

Reaction notes

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