2-Methoxybenzylamine → N-(2-methoxybenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

HRID 704241

Reaction equation

HRID 704241 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].Cl.[N:12]1([CH2:17][CH:18]([N:20]2[C:33]3[CH:32]=[C:31]([C:34](Cl)=[O:35])[CH:30]=[CH:29][C:28]=3[S:27][C:26]3[C:21]2=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH3:19])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:34]([C:31]1[CH:30]=[CH:29][C:28]2[S:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH:18]([CH3:19])[CH2:17][N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[C:33]=2[CH:32]=1)=[O:35]

Participants

4

Reactant 2

HCID 812922-MethoxybenzylamineHCID 2007488610-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride

Product 1

HCID 20074846N-(2-methoxybenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxybenzylamine (26.1 cc) is added dropwise at a temperature of 10° C. and with stirring to a solution of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride (13.2 g in methylene chloride (125 cc). Stirring is continued for 15 minutes at 10° C. and 16 hours at 20° C. The reaction mixture is washed with distilled water (3×100 cc) and the organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is purified by chromatography on a column (height: 64 cm; diameter: 3 cm) of silica gel (0.06-0.2 mm), eluting with ethyl acetate (2 liters) and collecting 200-cc fractions. Fractions 3 to 10 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give N-(2-methoxybenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (9.3 g) in the form of a white crystalline solid, m.p. 127° C.

Workup

  1. washThe reaction mixture is washed with distilled water (3×100 cc)
  2. dry with materialthe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  5. customThe residue is purified by chromatography on a column (height: 64 cm; diameter: 3 cm) of silica gel (0.06-0.2 mm)
  6. washeluting with ethyl acetate (2 liters)
  7. customcollecting 200-cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-f56686ee36e8432ebb42a5de56fafe5f
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Linked notes

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