Ammonium Chloride → HCID 178439601, compound

HRID 1453917Notes

Reaction equation

HRID 1453917 reaction equation
[Cl-:1].[NH4+:2].CO[C:5]1[CH:6]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]([CH2:10][CH2:11][CH3:12])[CH2:8][N:9]=1>C(O)C>[Cl-:1].[CH2:13]([CH:6]1[CH:7]([CH2:10][CH2:11][CH3:12])[CH2:8][NH:9][C:5]1=[NH2+:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 22928670HCID 22928670, compound

Product 1

HCID 178439601HCID 178439601, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ammonium chloride (155 mg, 2.9 mmol) was added to a solution of 4-benzyl-3-propyl-3,4-dihydro-2H-5-pyrrolyl methyl ether (0.67 g, 2.9 mmol) in ethanol (15 ml) and the mixture was heated to reflux for 4 hours. The reaction mixture was filtered and the filtrate was distilled off under reduced pressure. The residue was crystallized from ethyl acetate to yield the title compound (440 mg) as a white crude product. 1H-NMR (DMSO-d6) δ(ppm) 0.62 (3H, t, J=7.2 Hz), 0.87-1.20 (4H, m), 2.01-2.15 (1H, m), 2.72-2.85 (1H, m), 2.88-2.98 (1H, m), 3.05-3.25 (1H, m), 3.50-3.62 (1H, m), 7.19-7.40 (5H, m)

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationThe reaction mixture was filtered
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c16ee2508dc04df6bc850542be71efa5
Source dataset
uspto-grants-2009_01
Patent number
US07476688B2

Reaction notes

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