Hydrochloric Acid → Hydrochloric Acid

HRID 392161Notes

Reaction equation

HRID 392161 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][C@@H:16]2[O:30][C:20]3=[C:21]4[C:26](=[CH:27][CH:28]=[C:19]3[O:18][CH2:17]2)[N:25]=[C:24]([CH3:29])[CH:23]=[CH:22]4)=[CH:4][CH:3]=1.[C:31]([BH3-])#N.[Na+].[ClH:35]>C=O.C(O)(=O)C.CO.C(OCC)(=O)C.CCOCC>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][N:14]([CH3:31])[CH2:15][CH:16]2[O:30][C:20]3=[C:21]4[C:26](=[CH:27][CH:28]=[C:19]3[O:18][CH2:17]2)[N:25]=[C:24]([CH3:29])[CH:23]=[CH:22]4)=[CH:4][CH:3]=1.[ClH:35]

Participants

10

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 69366150HCID 69366150, compound

Product 2

HCID 313Hydrochloric AcidHCID 9979486HCID 9979486, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 712FormaldehydeSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [3-(6-fluoro-indol-1-yl)-propyl]-[(2S)-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl]-amine (0.53 g, 1.3 mmol) in 1.05 mL of formaldehyde, 0.11 mL of acetic acid and 20 mL of methanol was added to 95% sodium cyanoborohydride (0.13 g, 1.9 mmole). The mixture was allowed to stir at room temperature under nitrogen overnight. The mixture was partitioned between 400 mL each of methylene chloride and water. The organic portion was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was then column chromatographed on silica gel using 55% ethyl acetate/44% hexane/1% methanol as eluant. The product-containing fractions were concentrated under vacuum to give a yellow oil, which was dissolved in ethyl acetate and treated with excess HCl in ether to give 0.040 g of the (S)-enantiomer of the title compound as a yellow hydrochloride, m.p. 75.9-83.7° C.

Workup

  1. customThe mixture was partitioned between 400 mL each of methylene chloride and water
  2. washThe organic portion was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customcolumn chromatographed on silica gel using 55% ethyl acetate/44% hexane/1% methanol as eluant
  7. concentrationThe product-containing fractions were concentrated under vacuum
  8. customto give a yellow oil, which

Sources & evidence

ORD record
ord-ade7c25debe547f592a9bcb2ca045c79
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

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