4-(Aminosulfonyl)-3-thiophenecarbonyl chloride → 4-(Aminosulfonyl)-N-[3-[3-(1-piperidinylcarbonyl)phenoxy]propyl]-3-thiophene-carboxamide, hydrate

HRID 1731413Notes

Reaction equation

HRID 1731413 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:9]=[CH:10][CH:11]=1.[NH2:20][S:21]([C:24]1[C:25]([C:29](Cl)=[O:30])=[CH:26][S:27][CH:28]=1)(=[O:23])=[O:22]>O1CCCC1>[OH2:5].[NH2:20][S:21]([C:24]1[C:25]([C:29]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])[CH:7]=2)=[O:30])=[CH:26][S:27][CH:28]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 137325564-(Aminosulfonyl)-3-thiophenecarbonyl chlorideHCID 137325581-[[3-(3-Aminopropoxy)phenyl]carbonyl]piperidine

Product 1

HCID 1317149444-(Aminosulfonyl)-N-[3-[3-(1-piperidinylcarbonyl)phenoxy]propyl]-3-thiophene-carboxamide, hydrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.26 g. (0.001 mole) of 1-[[3-(3-aminopropoxy)phenyl]carbonyl]piperidine in 30 ml. of dry tetrahydrofuran is added 0.23 g. (0.001 mole) of 4-(aminosulfonyl)-3-thiophenecarbonyl chloride. The mixture is allowed to stand at room temperature for 15 minutes. The tetrahydrofuran is removed in a rotary evaporator and the residue is dissolved in 50 ml. of chloroform. The chloroform solution is extracted with 50 ml. of 10% aqueous sodium hydroxide solution followed by 50 ml. of 10% aqueous hydrochloric acid. The chloroform layer is washed with water, is dried over magnesium sulfate and is filtered. The filtrate is evaporated in a rotary evaporator to give 0.15 g. of an amorphous product, m.p. 70°-80° C.; mass spectrum CI m/e 452 MH+.

Workup

  1. customThe tetrahydrofuran is removed in a rotary evaporator
  2. dissolutionthe residue is dissolved in 50 ml
  3. extractionThe chloroform solution is extracted with 50 ml
  4. washThe chloroform layer is washed with water
  5. dry with materialis dried over magnesium sulfate
  6. filtrationis filtered
  7. customThe filtrate is evaporated in a rotary evaporator
  8. customto give 0.15 g

Sources & evidence

ORD record
ord-b9392de950984e5d9ebc3d61483ea14f
Source dataset
uspto-grants-1986_11
Patent number
US04621142

Reaction notes

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