Water → HCID 14986827, compound

HRID 1493456Notes

Reaction equation

HRID 1493456 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.[N:19]1[CH:24]=[CH:23][CH:22]=[N:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]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[CH2:29][CH2:30][N:25]([C:20]5[N:19]=[CH:24][CH:23]=[CH:22][N:21]=5)[CH2:26][CH2:27]4)[CH2:5]3)[CH2:2]1)[CH2:9]2

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 116802722-Piperazinylpyrimidine dihydrochlorideHCID 14986824HCID 14986824, compound

Product 1

HCID 14986827HCID 14986827, compoundYield 31%

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 (2.00 g, 6.99 mmol), 1-(2-pyrimidinyl)piperazine dihydrochloride (1.66 g, 7.00 mmol), diisopropylethylamine (3.6 mL, 21 mmol) in anhydrous dimethylformamide (100 mL) was heated at 60° C. for 23 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 into silica gel, and purified by flash chromatography (8 cm diameter, elution with 2.5% methanol in dichloromethane). The resulting solid was stirred over hexane for 2 hours and filtered to yield a beige solid (800 mg, 31%, m.p. 117°-119° 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, elution with 2.5% methanol in dichloromethane)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6776dbd8489d4628bce11e24825d1b9f
Source dataset
uspto-grants-1991_06
Patent number
US05021569

Reaction notes

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