O-Methyltyramine → HCID 737618, compound

HRID 2352304Notes

Reaction equation

HRID 2352304 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][NH2:22])=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][NH:22][S:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4657O-MethyltyramineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 737618HCID 737618, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Nitrobenzenesulphonyl chloride (10 g) was added portionwise to a stirred solution of 4-methoxyphenethylamine (6.8 g) in pyridine (40 ml) and the resulting solution stirred at room temperature for 30 min. The solution was partitioned between hydrochloric acid (5 N, 400 ml) and ethyl acetate (2×250 ml). The combined extracts were washed with hydrochloric acid (5 N, 100 ml), sodium bicarbonate (8%, 100 ml) dried --MgSO4) and evaporated in vacuo to give an oil. The oil was purified by column chromatography eluted with hexane:ethyl acetate (2:1) to give the title compound as a solid (4.7 g) m.p. 92°-93°.

Workup

  1. customThe solution was partitioned between hydrochloric acid (5 N, 400 ml) and ethyl acetate (2×250 ml)
  2. washThe combined extracts were washed with hydrochloric acid (5 N, 100 ml), sodium bicarbonate (8%, 100 ml)
  3. customdried
  4. customMgSO4) and evaporated in vacuo
  5. customto give an oil
  6. customThe oil was purified by column chromatography
  7. washeluted with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-4a6d41341ff14ea190d40122f53941c5
Source dataset
uspto-grants-1989_10
Patent number
US04876267

Reaction notes

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