Methanol → HCID 86600242, compound

HRID 2111852Notes

Reaction equation

HRID 2111852 reaction equation
Br.[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.Br[CH2:9][CH2:10][CH2:11][OH:12].[N+:13]([C:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=1)([O-])=O.CO.O.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(OCC)(=O)C>[S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)([OH:35])(=[O:34])=[O:33].[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][CH2:11][O:12][C:19]1[CH:20]=[CH:21][C:16]([NH2:13])=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 9804-NitrophenolHCID 123083-Bromo-1-propanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 12444175(2R)-2-methylpyrrolidine hydrobromide2×

Product 1

HCID 86600242HCID 86600242, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}aniline was obtained as a light brown oily substance by the method according to Example 138, using (2R)-2-methylpyrrolidine hydrobromide, 3-bromopropanol and 4-nitrophenol as starting materials. The obtained oily substance was dissolved in ethyl acetate, 1 Eq of a methanol solution of p-toluenesulfonic acid monohydrate was added, and the target compound was obtained as a colorless solid by filtering off the solid produced. (2R)-2-methylpyrrolidine hydrobromide was manufactured by the method described in the literature (J. Org. Chem., 1989, Vol. 54, p. 209)

Workup

  1. customthe target compound was obtained as a colorless solid
  2. filtrationby filtering off the solid
  3. customproduced

Sources & evidence

ORD record
ord-b8ac1dbdd4444d7986f6c1f19cb47f9e
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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