Formaldehyde → 1-(3-Fluoro-benzyl)-4-(1-methyl-piperidin-4-yl)-1H-indole-2-carboxylic acid amide

HRID 18165

Reaktionsgleichung

Reaktionsgleichung von HRID 18165
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:21]([NH2:23])=[O:22].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:31](C)=O.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH:15]3[CH2:20][CH2:19][N:18]([CH3:31])[CH2:17][CH2:16]3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:21]([NH2:23])=[O:22]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 249523631-(3-Fluoro-benzyl)-4-piperidin-4-yl-1H-indole-2-carboxylic acid amide

Produkt 1

HCID 249530691-(3-Fluoro-benzyl)-4-(1-methyl-piperidin-4-yl)-1H-indole-2-carboxylic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-Fluoro-benzyl)-4-piperidin-4-yl-1H-indole-2-carboxylic acid amide (50 mg, 0.14 mmol) in CH2Cl2 (5 ml) were added formaldehyde (20 μl, 0.24 mmol, 37% in H2O solution) and NaBH(OAc)3 (74 mg, 0.35 mmol). After stirring at room temperature for 4 hours, the reaction mixture was added to a saturated solution of sodium bicarbonate, followed by a mixture of CH2Cl2/H2O. The organic fraction was separated, washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo to give 1-(3-Fluoro-benzyl)-4-(1-methyl-piperidin-4-yl)-1H-indole-2-carboxylic acid amide as a brown oil. This oil was dissolved in 4 ml ethanol, and 2 M ethanolic hydrochloric acid solution (1 ml) was added. The reaction mixture is heated at 100° C. for 20 minutes, then cooled to room temperature, and 14 mg of 1-(3-Fluoro-benzyl)-4-(1-methyl-piperidin-4-yl)-1H-indole-2-carboxylic acid amide hydrochloride salt was collected. MS: 366 (M+H)+.

Aufarbeitung

  1. customThe organic fraction was separated
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic fraction was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8ed52b147ee24242aaa6738f3761994a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741326B2

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