Hydrochloric Acid → HCID 59856530, compound

HRID 2378956Notes

Reaction equation

HRID 2378956 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[N+:24]([O-:26])=[O:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Si](C)(C)C.[BH4-].[Li+].O.Cl.[OH-].[Na+]>O1CCCC1>[F:23][C:19]1[C:18]([N+:24]([O-:26])=[O:25])=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][CH2:15][NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 59856527HCID 59856527, compound

Product 1

HCID 59856530HCID 59856530, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N-(1-Benzylpiperidin-4-yl)-2-(3-fluoro-2-nitrophenyl)acetamide (2.19 g, 5.90 mmol) was dissolved in tetrahydrofuran (40 ml). Mixture was warmed to 60° C. Chlorotrimethylsilane (2.7 ml, 21.27 mmol) was added to the mixture followed by lithium borohydride (7.2 ml, 14.40 mmol). Mixture was held at 60° C. for 2 hours with stirring. Reaction was quenched with 2 mL methanol. Water (4.0 ml, 222 mmol) was added to the mixture followed by concentrated hydrochloric acid (4.0 ml, 47.4 mmol). Mixture was warmed to reflux and held with stirring for 3 hours. Mixture was cooled to room temperature. Reaction was made basic with 5 mL 10N sodium hydroxide. Mixture stirred at room temperature for 15 minutes. Reaction layers were partitioned and the aqueous phase was discarded. Organic phase was concentrated by roto-vap. Silica gel chromatography eluting 2M ammonia in methanol-dichloromethane afforded the title compound as grey oil in 38% yield. MS (M+H)+=358.4.

Workup

  1. customReaction
  2. customwas quenched with 2 mL methanol
  3. temperatureMixture was warmed
  4. temperatureto reflux
  5. stirringwith stirring for 3 hours
  6. temperatureMixture was cooled to room temperature
  7. customReaction
  8. stirringMixture stirred at room temperature for 15 minutes
  9. customReaction layers
  10. customwere partitioned
  11. concentrationOrganic phase was concentrated by roto-vap
  12. washSilica gel chromatography eluting 2M ammonia in methanol-dichloromethane

Sources & evidence

ORD record
ord-ec75ca3039fb46eeb1a3c0c6118a68fa
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

Loading…