4-Fluorobenzaldehyde → HCID 67002067, compound

HRID 2279223Notes

Reaction equation

HRID 2279223 reaction equation
[CH2:1]1[N:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[CH2:9][NH:10][C:11](=[O:12])[CH:5]2[CH2:4][NH:3][CH2:2]1.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>CO>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:3]2[CH2:2][CH2:1][N:6]3[C:7]4[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=4[CH2:9][NH:10][C:11](=[O:12])[CH:5]3[CH2:4]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67001076HCID 67001076, compound

Product 1

HCID 67002067HCID 67002067, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3,4,4a,6,7-Hexahydropyrazino[1,2-a][1,4]benzodiazepin-5(1H)-one (680.0 mg, 3.13 mmol, Example 2A) was dissolve in methanol (15 mL). 4-Fluorobenzaldehyde (653.5 mg, 5.27 mmol) was added to the reaction and stirred at ambient temperature for 1 hour. Sodium cyanoborohydride (565.3 mg, 9.00 mmol) was then added, and the reaction was stirred at ambient temperature for 17 hours. The reaction was then diluted with 1 MNaOH (50 mL) and extract with dichloromethane (3×50 mL). The organic layers were combined, and purified by silica gel chromatography (ethyl acetate, Rf 0.40) to give the title compound: 1H NMR (400 MHz, benzene-d6) δ ppm 1.93 (td, J=11.0, 2.8 Hz, 1H), 2.42 (t, J=10.6 Hz, 1H), 2.49-2.51 (m, 1H), 2.60 (dt, J=11.0, 2.6 Hz, 1H), 2.85 (td, J=11.2, 2.9 Hz, 1H), 3.02-3.10 (m, 2H), 3.30 (d, J=13.2 Hz, 1H), 3.50 (dt, J=10.7, 2.3 Hz, 1H), 3.75 (dd, J=10.4, 2.8 Hz, 1H), 4.51 (dd, J=13.6, 4.0 Hz, 1H), 6.72-6.73 (d, J=8.1 Hz, 1H), 6.75 (dd, J=7.3, 1.5 Hz, 1H), 6.81-6.84 (m, 3H), 7.02-7.09 (m, 3H); MS (DCI/NH3) m/z 326 (M+H)+.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 17 hours
  2. additionThe reaction was then diluted with 1 MNaOH (50 mL)
  3. extractionextract with dichloromethane (3×50 mL)
  4. custompurified by silica gel chromatography (ethyl acetate, Rf 0.40)

Sources & evidence

ORD record
ord-3754b8c7f71e4a3ea2c9132d97a0180c
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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