Water → HCID 14986825, compound

HRID 1493455Notes

Reaction equation

HRID 1493455 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:3]([N:4]([C:12](=[O:16])[CH2:13][CH2:14]Br)[CH2:5]3)[CH2:2]1)[CH2:9]2.Cl.[Cl:18][C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:3]([N:4]([C:12](=[O:16])[CH2:13][CH2:14][N:28]4[CH2:27][CH2:26][N:25]([C:21]5[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[CH:20]=5)[CH2:30][CH2:29]4)[CH2:5]3)[CH2:2]1)[CH2:9]2

Participants

6

Reactant 4

HCID 962WaterHCID 256811-(3-Chlorophenyl)piperazine monohydrochlorideHCID 81531DiisopropylethylamineHCID 14986824HCID 14986824, compound

Product 1

HCID 14986825HCID 14986825, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-azatricyclo[4.3.1.1(3,8)]undec-4-yl)-3-bromo-1-propanone (1.96 g, 6.8 mmol), 1-(3-chlorophenyl)piperazine hydrochloride (1.60 g, 6.8 mmol) and diisopropylethylamine (2.4 mL, 14 mmol) in anhydrous dimethylformamide (100 mL) was heated at 60° C. for 19 hours. The reaction mixture was poured into water (700 mL) and extracted with ethyl acetate (2×200 mL). The combined organic layers were dried, preadsorbed onto silica gel, and purified by flash chromatography (8 cm diameter, gradient elution with 2-5% methanol in dichloromethane). The resulting solid was recrystallized from ethyl acetate in hexane to yield a light tan solid (1.4 g, 51%, m.p. 110°-112° C.).

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. customThe combined organic layers were dried
  3. custompurified by flash chromatography (8 cm diameter, gradient elution with 2-5% methanol in dichloromethane)
  4. customThe resulting solid was recrystallized from ethyl acetate in hexane

Sources & evidence

ORD record
ord-34427f5079fb4678a176021da802730c
Source dataset
uspto-grants-1991_06
Patent number
US05021569

Reaction notes

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