Hydrochloric Acid → 4-(2,3-dihydro-1H-isoindol-5-yl)-1-methyl-piperidin-4-ol dihydrochloride

HRID 334970

Reaktionsgleichung

Reaktionsgleichung von HRID 334970
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][N:13](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:12]3)([OH:8])[CH2:4][CH2:3]1.[ClH:37]>CO>[ClH:37].[ClH:37].[CH2:14]1[C:15]2[C:11](=[CH:10][C:9]([C:5]3([OH:8])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:17][CH:16]=2)[CH2:12][NH:13]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 592631371-methyl-4-(2-trityl-2,3-dihydro-1H-isoindol-5-yl)-piperidin-4-ol

Produkt 1

HCID 666725264-(2,3-dihydro-1H-isoindol-5-yl)-1-methyl-piperidin-4-ol dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-methyl-4-(2-trityl-2,3-dihydro-1H-isoindol-5-yl)-piperidin-4-ol (1.42 g, 3.0 mmol), 5N hydrochloric acid (5 mL) and methanol (10 mL) was placed under nitrogen then heated to reflux for 80 minutes. After cooling, the mixture was concentrated in vacuo to remove methanol, diluted with water and washed with ethyl acetate (×2). The aqueous phase was concentrated to dryness to afford the title compound in quantitative yield as a black solid. 1H NMR (MeOH-d4) 7.62 (1H, s), 7.57 (1H, d), 7.45 (1H, d), 4.64 (2H, s), 4.63 (2H, s), 3.49-3.46 (4H, m), 2.95 (3H, s), 2.40-2.32 (2H, m), 1.97 (2H, dd).

Aufarbeitung

  1. temperaturethen heated
  2. temperatureto reflux for 80 minutes
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. customto remove methanol
  6. additiondiluted with water
  7. washwashed with ethyl acetate (×2)
  8. concentrationThe aqueous phase was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3c19a17a6f0d45d38950d4f632a3ee31
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883790B2

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