Hydrochloric Acid → HCID 59429324, compound

HRID 505714Notes

Reaction equation

HRID 505714 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].[CH:16]1([CH:21]=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.N1CCCC1.Cl>CO>[CH:16]1(/[CH:21]=[C:10]2/[C:11](=[O:15])[C:12]3[CH:13]=[CH:14][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][C:7]=3[CH2:8][CH2:9]/2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 70106CyclopentanecarbaldehydeHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

Product 1

HCID 59429324HCID 59429324, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 6-acetamido-1-tetralone (200 mg, 0.98 mmol) and cyclopentanecarboxaldehyde (0.21 mL, 1.9 mmol) in methanol (2 mL) was treated with pyrrolidine (0.25 mL, 2.9 mmol) at room temperature for 1 hour then heated at 55° C. overnight. The mixture was cooled to room temperature, treated with 1N Hydrogen chloride (4 mL) was filtered thru a Chem Elute tube (CE101 1) eluting with 90% dichloromethane/10% ethyl acetate and condensed filtrate to give (E)-N-(6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (200 mg, 0.71 mmol, 72% n yield) as a tan foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25-1.44 (m, 2H), 1.52-1.76 (m, 4H), 1.77-1.90 (m, 2H), 2.08 (s, 3H), 2.70-2.92 (m, 5H), 6.63 (d, J=9.67 Hz, 1H), 7.49 (dd, J=8.59, 2.15 Hz, 1H), 7.59-7.66 (m, 1H), 7.86 (d, J=8.59 Hz, 1H), 10.23 (s, 1H). ES-MS m/z 284 (M+H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationwas filtered
  3. washElute tube (CE101 1)
  4. washeluting with 90% dichloromethane/10% ethyl acetate and condensed filtrate

Sources & evidence

ORD record
ord-99e75e3b3aee40c4a92cda4ab339d121
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

Loading…