Hydrochloric Acid → HCID 15029887, compound

HRID 847259Notes

Reaction equation

HRID 847259 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13](=O)[CH3:14])[CH2:8][CH2:7][CH2:6]2.[CH2:16]([NH2:18])[CH3:17].Cl.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH:13]([NH:18][CH2:16][CH3:17])[CH3:14])[CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 15029879HCID 15029879, compound

Product 1

HCID 15029887HCID 15029887, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 93 (2 g) was dissolved in anhydrous MeOH (20 ml) and EtNH2 (3 ml) and the pH adjusted to ca. 8 with methanolic HCl. Sodium cyanoborohydride (500 mg) was added and an additional 2 ml methanolic HCl dropwise. The reaction was stirred under N2 for 48h then 6 N HCl added to pH<2. The methanol was removed under vacuum and the aqueous layer extracted with CH2Cl2 (2×100 ml). The organic layer was separated, washed with brine, dried (MgSO4), filtered and evaporated giving 0.18 g of an oil. The neutral CH2Cl2 extract was dried (MgSO4), filtered and evaporated then partitioned between 2 N HCl and a mixture of ether/hexane. The organic layer was separated and discarded. The acidic layer was basified and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and evaporated giving an additional 1.12 g of product.

Workup

  1. customThe methanol was removed under vacuum
  2. extractionthe aqueous layer extracted with CH2Cl2 (2×100 ml)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7292446cbebf470296e1277d31194fac
Source dataset
uspto-grants-1992_08
Patent number
US05140040

Reaction notes

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