Toluene → HCID 58999558, compound

HRID 1593369Notes

Reaction equation

HRID 1593369 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.Cl[CH2:28][CH:29]=[CH:30][CH2:31][OH:32].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:28]/[CH:29]=[CH:30]\[CH2:31][OH:32])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 70048BenzhydrylpiperazineHCID 81531DiisopropylethylamineHCID 53394963HCID 53394963, compound

Product 1

HCID 58999558HCID 58999558, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

A solution containing 1-benzhydrylpiperazine (3 g, 0.0119 mol), toluene (20 ml), 4-chloro-2-butene-1-ol (1.65 g, 0.0155 mol), diisopropylethylamine (3.81 g, 0.0295 mol), and DMF (3 ml) is stirred at 55-60° C. for 5 hrs. The reaction mass is quenched with water (20 ml), organic layer separated and the aqueous layer extracted with dichloromethane (2×20 ml). The organic extract is washed with water (10 ml), and concentrated to obtain crude product, which is purified by flash column chromatography on silica gel using dichloromethane-methanol (9.3:0.7) as mobile phase to obtain pure product.

Workup

  1. customThe reaction mass is quenched with water (20 ml), organic layer
  2. customseparated
  3. extractionthe aqueous layer extracted with dichloromethane (2×20 ml)
  4. extractionThe organic extract
  5. washis washed with water (10 ml)
  6. concentrationconcentrated
  7. customto obtain crude product, which
  8. customis purified by flash column chromatography on silica gel
  9. customto obtain pure product

Sources & evidence

ORD record
ord-d52cdcc69d21472a9c722b8cc464690c
Source dataset
uspto-grants-2007_11
Patent number
US07297697B2

Reaction notes

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