Isopropanol → HCID 14581387, compound

HRID 329411Notes

Reaction equation

HRID 329411 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH2:12])=[CH:7][CH:6]=[CH:5]2.[CH2:13]([N:20]([CH2:24][CH2:25]Cl)[CH2:21][CH2:22]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C.C(O)(C)C>C(OCC)(=O)C>[CH2:13]([N:20]1[CH2:24][CH2:25][N:12]([C:8]2[C:9]3[C:4](=[CH:3][C:2]([F:1])=[CH:11][CH:10]=3)[CH:5]=[CH:6][CH:7]=2)[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 5928N-BenzylnormechlorethamineHCID 81531DiisopropylethylamineHCID 14581386HCID 14581386, compound

Product 1

HCID 14581387HCID 14581387, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.0 g (6.21 mmol) of 6-fluoro-1-amino naphthalene, 1.8 g (7.76 mmol) of N-benzyl bis(2-chloroethyl)amine, 3.3 ml (19.2 mmol) of diisopropylethylamine, and 50 ml isopropanol. The reaction was refluxed 24 hours, cooled, and evaporaated to an oil. The oil was taken up in ethyl acetate, washed with waterand brine, dried over sodium sulfate, and evaporated to an oil. The oil was chromatographed on silica gel using methylene chloride as eluent to afford 1.5 g (75.5%) of an oil.

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 24 hours
  3. temperaturecooled
  4. washwashed with waterand brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to an oil
  7. customThe oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-2423f14ee17a4335a30867da8a4288f1
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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