Hydrochloric Acid → 2-{4-[(Dimethylamino)methyl]phenyl}-3,10-diazatricyclo[6.4.1.0^{4,13}]trideca-1,4(13),5,7-tetraen-9-one

HRID 489513

Reaktionsgleichung

Reaktionsgleichung von HRID 489513
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][C:17]=2[C:16]=34)=[CH:5][CH:4]=1)=O.[CH3:23][NH:24][CH3:25].C([BH3-])#N.[Na+].Cl>CO.[Cl-].[Zn+2].[Cl-]>[CH3:23][N:24]([CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][C:17]=2[C:16]=34)=[CH:5][CH:4]=1)[CH3:25]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 117482882-(4-formylphenyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one

Produkt 1

HCID 109801192-{4-[(Dimethylamino)methyl]phenyl}-3,10-diazatricyclo[6.4.1.0^{4,13}]trideca-1,4(13),5,7-tetraen-9-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

The aldehyde (310 mg, 1.07 mmol) in MeOH (40 mL) was treated with dimethyl amine (2M solution in MeOH, 6.41 mmol). The solution was cooled with an ice/water bath and treated dropwise with a solution of sodium cyanoborohydride (74 mg, 1.18 mmol) and zinc chloride (80 mg, 0.59 mmol) in MeOH (10 mL). The resulting solution was adjusted to pH=6-7 with 2M methanolic HCl. After stirring for 30 min., the reaction was quenched with conc. HCl (0.2 mL) and the methanol was removed by evaporation. The residue was diluted with water (30 mL). The solution adjusted to pH=10-11 with KOH (s) and extracted with CH2Cl2 (30 mL×3). The organic solution was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The crude product was crystallized (CH2Cl2/MeOH/hexanes) to give 2-(4-(N,N-dimethylamino)methylphenyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one, 245 mg (72%), as an off-white solid. mp 226-229° C. (dec.); 1H NMR (300 MHz, d6-DMSO) δ 2.18 (s, 6H), 3.06 (m, 2H), 3.40 (m, 2H), 3.44 (s, 2H), 7.21 (t, 1H, J=7.7 Hz), 7.43 (d of ABq, 2H, J=7.9 Hz), 7.56 (d, 1H, J=7.7 Hz), 7.61 (d of ABq, 2H, J=7.9 Hz), 7.69 (d, 1H, J=7.7 Hz), 8.05 (br t, 1H), 11.53 (br s, 1H); HRMS (FAB, MH+) Calcd for C20H22N3O: 320.1763; Found: 320.1753; Anal. (C20H21N3O.0.55H2O) C, H, N.

Aufarbeitung

  1. temperatureThe solution was cooled with an ice/water bath
  2. customthe reaction was quenched with conc. HCl (0.2 mL)
  3. customthe methanol was removed by evaporation
  4. additionThe residue was diluted with water (30 mL)
  5. extractionextracted with CH2Cl2 (30 mL×3)
  6. washThe organic solution was washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was crystallized (CH2Cl2/MeOH/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fa11e97b6d3b4d45a0e8c43a6a493e9f
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977298B2

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