3-Phenylpropylamine → HCID 21993759, compound

HRID 1978321Notes

Reaction equation

HRID 1978321 reaction equation
[O:1]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]O)=[C:22]([CH2:28]O)[CH:21]=1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[C:44]1([CH2:50][CH2:51][CH2:52][NH2:53])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(#N)C>[O:1]([CH2:19][C:20]1[CH:21]=[C:22]2[C:23](=[CH:24][CH:25]=1)[CH2:26][N:53]([CH2:52][CH2:51][CH2:50][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:28]2)[Si:2]([C:15]([CH3:18])([CH3:16])[CH3:17])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 162593-PhenylpropylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21994041HCID 21994041, compound

Product 1

HCID 21993759HCID 21993759, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5.867 g (14.429 mM) of [4-(tert-butyldiphenylsiloxymethyl)-2-hydroxymethylphenyl]methanol and 12.6 ml (72.1 mM) of N,N-diisopropylethylamine in 100 ml of acetonitrile was added a solution of 3.47 g (30.3 mM) of methanesulfonyl chloride in 10 ml of acetonitrile dropwise with ice-cooling and the mixture was stirred at 0° C. for 0.5 hour. To this reaction mixture was added 2.15 g (15.9 mM) of 3-phenylpropylamine and the mixture was stirred at 80° C. overnight. The solvent was then distilled off under reduced pressure and the residue was diluted with aqueous solution of sodium hydrogen carbonate and extracted with 3 portions of ethyl acetate. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to provide the title compound.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 80° C. overnight
  3. distillationThe solvent was then distilled off under reduced pressure
  4. additionthe residue was diluted with aqueous solution of sodium hydrogen carbonate
  5. extractionextracted with 3 portions of ethyl acetate
  6. dry with materialThe pooled organic layer was dried over MgSO4
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Sources & evidence

ORD record
ord-d0125f2f22d1487e8628d1407906a6b9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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