N-Methylphenylethanolamine → HCID 21842621, compound

HRID 1737450Notes

Reaction equation

HRID 1737450 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>C1COCC1>[OH:11][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][N:2]([CH3:1])[S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 913N-MethylphenylethanolamineHCID 7369Benzenesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 21842621HCID 21842621, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of α-(methylaminomethyl)benzyl alcohol (1.00 g, 6.61 mmol) in 15 mL of THF was cooled in an ice bath. Benzenesulfonyl chloride (0.886 mL, 1.23 g, 6.94 mmol) and N,N-diisopropylethylamine (2.3 mL, 1.7 g, 13 mmol) were added and mixture was allowed to warm to room temperature. After 30 min, the solvent was evaporated and the residue was partitioned between 50 mL of ethyl acetate and 40 mL of saturated aqueous sodium bicarbonate. The aqueous layer was extracted with 2×50 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried over sodium sulfate, and evaporated. Purification by flash column chromatography on silica gel, eluting with 20-50% ethyl acetate in hexane, gave the title compound in quantitative yield.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between 50 mL of ethyl acetate and 40 mL of saturated aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with 2×50 mL of ethyl acetate
  4. washThe combined organic layers were washed with 50 mL of brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by flash column chromatography on silica gel
  8. washeluting with 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ba598985bff041bf90162b74bd66b628
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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