Hydrochloric Acid → HCID 69948262, compound

HRID 609744Notes

Reaction equation

HRID 609744 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.[BH3-]C#N.[Na+].Cl>C(O)C>[N:18]1([CH2:17][CH2:16][C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)[CH:8]=3)[NH:12][CH:11]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 69948801HCID 69948801, compound

Product 1

HCID 69948262HCID 69948262, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(2,3-dihydropyran-2-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 20b, 0.049 g, 0.165 mmol) in absolute ethanol (5 mL) was added NaBH3CN (0.496 mmol) and methanolic HCl [prepared from acetyl chloride (2 mL) and methanol (10 mL)] alternately. The mixture was allowed to stir for 3 hours at which time the reaction was quenched with sodium bicarbonate (sat.) and the product was extracted three times with CH2Cl2. The organic layer was dried (NaSO4), filtered and concentrated. The crude product was purified by column chromatography (7% NH3 in CH2Cl2) to yield the title compound 0.029 g, 59%) as a clear oil; HRMS-FAB+ for C19H26N2O: calc. MH+ : 99.2123; found MH+ :299.2159.

Workup

  1. customwas quenched with sodium bicarbonate (sat.)
  2. extractionthe product was extracted three times with CH2Cl2
  3. dry with materialThe organic layer was dried (NaSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (7% NH3 in CH2Cl2)

Sources & evidence

ORD record
ord-10412ca87f3d4419ae105e99f1d453d7
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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