o-Methylvalerolactim → 1-(4-Fluorophenyl)-1-{3-[methyl(3,4,5,6-tetrahydropyridin-2-yl)amino]propyl}-1,3-dihydro-2-benzo-furan-5-carbonitrile

HRID 1754235Notes

Reaction equation

HRID 1754235 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][C:6]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13]([C:15]#[N:16])=[CH:14][C:9]=2[CH2:8][O:7]1.CO[C:26]1[CH2:27][CH2:28][CH2:29][CH2:30][N:31]=1>>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:6]2([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[C:26]3[CH2:27][CH2:28][CH2:29][CH2:30][N:31]=3)[C:10]3[CH:11]=[CH:12][C:13]([C:15]#[N:16])=[CH:14][C:9]=3[CH2:8][O:7]2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 138567o-MethylvalerolactimHCID 162180Desmethylcitalopram

Product 1

HCID 1184612951-(4-Fluorophenyl)-1-{3-[methyl(3,4,5,6-tetrahydropyridin-2-yl)amino]propyl}-1,3-dihydro-2-benzo-furan-5-carbonitrile

Conditions

Temperature
80 °C

Procedure

A mixture of 0.200 g (0.64 mmol) of 1-[3-(methylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (Preparation 1) and 6-methoxy-2,3,4,5-tetrahydropyridine (0.080 g, 0.71 mmol, 1.1 equiv.) was heated at 80° C. for 15 hr, cooled to rt and concentrated in vacuo to a gummy residue. The crude product was purified using column chromatography to give the title product as an off-white solid, 0.060 g (24%).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo to a gummy residue
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-9724191188974a8cb16b562feb17dc70
Source dataset
uspto-grants-2015_10
Patent number
US09169237B1

Reaction notes

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