Formic Acid → HCID 22034196, compound

HRID 130340Notes

Reaction equation

HRID 130340 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[CH:11](O)=[O:12].Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:11]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2)=[O:12]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 81531DiisopropylethylamineHCID 90496Indan-5-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22034196HCID 22034196, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-aminoindane (7.53 g, 56.5 mmol) in DMF (100 mL) was added formic acid (2.2 mL, 58.3 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (10.94 g, 57 mmol) and diisopropylethylamine (19.7 mL, 0.11 mol). The resulting solution was stirred overnight and then partitioned between saturated aqueous citric acid (100 mL) and ethyl acetate (200 mL). The organic layer was separated and washed with aqueous sodium bicarbonate solution (100 mL) and water (3×100 mL), then concentrated under reduced pressure to give the formamide as a thick oily solid (8.5 g, 93%).

Workup

  1. custompartitioned between saturated aqueous citric acid (100 mL) and ethyl acetate (200 mL)
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium bicarbonate solution (100 mL) and water (3×100 mL)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cc1c9332e4c439b912a3e2315acc014
Source dataset
uspto-grants-2008_06
Patent number
US07381734B2

Reaction notes

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