Hydrochloric Acid → HCID 20094419, compound

HRID 744695Notes

Reaction equation

HRID 744695 reaction equation
[ClH:1].[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)=[O:20].C=O.[C:34]([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+].Cl>CO.C(O)C.C(OCC)(=O)C>[ClH:1].[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[CH2:12][N:13]([CH3:34])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:26][CH:27]=1)=[O:20]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 19422064HCID 19422064, compound

Product 1

HCID 20094419HCID 20094419, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methylamino]-N-[4-(trifluoromethyl)phenyl]hexanamide monohydrochloride (201 mg), 37% aqueous formaldehyde (0.18 mL) and sodium cyanoborohydride (38 mg) were stirred in methanol (4.8 mL) for 96 hours at 20°-25° C. under nitrogen atmosphere. Saturated sodium bicarbonate (20 mL) was added to the reaction and extracted with dichloromethane (2×20 mL). The combined extracts were dried (Na2SO4) and concentrated vacuo. The resulting oil was chromatographed eluting with ethyl acetate and 10:90 ethanol:ethyl acetate to give a white solid (Rf of 0.52 in 10:90 ethanol:ethyl acetate) which was dissolved in ethanol and treated with 1.0M aqueous HCl (1 ml). The solution was concentrated in vacuo to give an oil which was dissolved in 70:30 ethyl acetate:hexane and concentrated. A hygroscopic white solid (151 mg) remained. CIMS (CH4): 437 (100%), 301 (40%). Exact Mass (CIMS, CH4): Calc. for C23H23F3N2O3 :437.2052. Found: 437.2044.

Workup

  1. extractionextracted with dichloromethane (2×20 mL)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated vacuo
  4. customThe resulting oil was chromatographed
  5. washeluting with ethyl acetate and 10:90 ethanol
  6. customethyl acetate to give a white solid (Rf of 0.52 in 10:90 ethanol:ethyl acetate) which
  7. concentrationThe solution was concentrated in vacuo
  8. customto give an oil which
  9. concentrationhexane and concentrated

Sources & evidence

ORD record
ord-bea9597cf60045f28a8cd176e1c098a7
Source dataset
uspto-grants-1996_09
Patent number
US05559143

Reaction notes

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