Water → 1-[3-(4-(4-Hydroxyphenyl)-1-piperazinyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide

HRID 654098Notes

Reaction equation

HRID 654098 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH2:10][CH2:9][CH2:8][N:7]3[S:6]1(=[O:18])=[O:17].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[OH:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][N:5]3[C:15]4=[C:16]5[C:11](=[CH:12][CH:13]=[CH:14]4)[CH2:10][CH2:9][CH2:8][N:7]5[S:6]3(=[O:18])=[O:17])[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 92467p-(1-Piperazinyl)phenolHCID 198884501-(3-chloropropyl)-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide

Product 1

HCID 198884561-[3-(4-(4-Hydroxyphenyl)-1-piperazinyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxideYield 46.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(3-chloropropyl)-5,6-dihydro-(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (4 g), 4-(4-hydroxyphenyl)piperazine (4.75 g) and triethylamine (5.88 cc) in dry N,N-dimethylformamide (50 cc) is heated to reflux for 90 minutes and is then cooled and poured into a mixture of water (300 cc) and ethyl acetate (300 cc). The organic phase is washed with water (3×200 cc), is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The solid is recrystallized from ethyl acetate (300 cc) and dried. 1-[3-(4-(4-Hydroxyphenyl)-1-piperazinyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (2.8 g) is obtained, melting at 182° C.

Workup

  1. temperatureto reflux for 90 minutes
  2. temperatureis then cooled
  3. washThe organic phase is washed with water (3×200 cc)
  4. dry with materialis dried over magnesium sulphate
  5. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe solid is recrystallized from ethyl acetate (300 cc)
  7. customdried

Sources & evidence

ORD record
ord-bf500393758f42a3b26cc10d8ce9ac88
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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