Formic Acid → HCID 20203550, compound

HRID 1732064Notes

Reaction equation

HRID 1732064 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH3:11][CH:12]([NH:14][CH:15]1[C:20]2=[C:21]([CH3:28])[C:22]3[C:27]([N:19]2[CH2:18][CH2:17][CH2:16]1)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:13]>O1CCCC1>[CH3:28][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]2[CH2:18][CH2:17][CH2:16][CH:15]([N:14]([CH:12]([CH3:13])[CH3:11])[CH:1]=[O:3])[C:20]=12

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 13749170HCID 13749170, compound

Product 1

HCID 20203550HCID 20203550, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of formic acid (6 mL) and acetic anhydride (12 mL) was heated at 60° C. for 4 hours. A solution of 6,7,8,9-tetrahydro-N-(1-methylethyl)-10-methylpyrido[1,2-a]indol-9-amine (6 g, 24.7 mmol, described in Example 22) in tetrahydrofuran (60 mL) was added at once at 25° C. under exclusion of moisture. The reaction mixture was stirred at 25° C. for 12 hours, then poured into ice water (120 mL). The product was extracted with ether (3×80 mL), and the combined organic layer washed with 5% HCl, 10% NaHCO3, and water. The separated organic layer was dried over MgSO4, filtered, and evaporated to afford 6 g (90%) of the title compound as an amber oil.

Workup

  1. extractionThe product was extracted with ether (3×80 mL)
  2. washthe combined organic layer washed with 5% HCl, 10% NaHCO3, and water
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6dd88df1d0a24c29a5a958d71d6ddd36
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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