Formic Acid → HCID 20203540, compound

HRID 1732061Notes

Reaction equation

HRID 1732061 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.Cl.[CH3:12][NH:13][CH:14]1[C:19]2=[C:20]([CH3:27])[C:21]3[C:26]([N:18]2[CH2:17][CH2:16][CH2:15]1)=[CH:25][CH:24]=[CH:23][CH:22]=3>O1CCCC1>[CH3:27][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:18]2[CH2:17][CH2:16][CH2:15][CH:14]([N:13]([CH3:12])[CH:1]=[O:3])[C:19]=12

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 13749169HCID 13749169, compound

Product 1

HCID 20203540HCID 20203540, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Formic acid (7 mL) and acetic anhydride (14 mL) were mixed and heated at 60° C. for 4 hours. A solution of 6,7,8,9-tetrahydro-N,10-dimethylpyrido[1,2-a]indol-9-amine hydrochloride (7.49 g, 35 mmol) in tetrahydrofuran (40 mL) was added, and the mixture was stirred at room temperature overnight. The resultant solution was poured onto ice, and products were extracted with ether. The combined extracts were washed with 5% hydrochloric acid, 5% bicarbonate, and water. After drying (MgSO4) and filtration, the solvent was removed, and the residual oil was rapidly filtered through a silica gel column packed in chloroform/methanol 50:1. The title formamide was obtained as a yellowish oil 6.3 g (74%).

Workup

  1. extractionwere extracted with ether
  2. washThe combined extracts were washed with 5% hydrochloric acid, 5% bicarbonate, and water
  3. customAfter drying
  4. filtration(MgSO4) and filtration
  5. customthe solvent was removed
  6. filtrationthe residual oil was rapidly filtered through a silica gel column

Sources & evidence

ORD record
ord-4a4516301718445d99692c304c529aa4
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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