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4-Fluorobenzoyl chloride → 8-Methoxy-2-(2-(4-fluorobenzamido)ethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

HRID 5349
Notes
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Reaction equation

HRID 5349 reaction equation
[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][CH2:16][NH2:17])[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:25])=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl.C(N(CC)CC)C>[ClH:25].[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][CH2:16][NH:17][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=3)[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 197956898-Methoxy-2-(2-aminoethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 197956978-Methoxy-2-(2-(4-fluorobenzamido)ethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471Triethylamine
Solvent

Conditions

Temperature
-20 °C

Procedure

The product from Example 17 (0.95 g) was dissolved in 50 ml methylene chloride and 1.5 ml triethyl amine. The solution was cooled to -20° C. and 0.59 ml p-fluorobenzoyl chloride was added. After 30 min, the reaction was quenched in 5% NaHCO3 and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), evaporated, and the product was dissolved in ether and treated with ethereal HCl and then evaporated to dryness. The resulting product was recrystallized from ethyl acetate and ether to yield 0.772 g of the desired product as a white solid, mp: 197°-8° C. NMR (d6DMSO) δ2.60-3.10 (m, 3H), 3.00-3.50 (m, 4H), 3.59 (m, 2H), 3.78 (s, 3H), 3.82-4.22 (m, 3H), 6.83 (d, 1H), 6.87 (d, 1H), 7.23 (t, 1H), 7.34 (m, 2 H), 8.00 (m, 2H).

Workup

  1. customthe reaction was quenched in 5% NaHCO3
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. customevaporated
  5. dissolutionthe product was dissolved in ether
  6. additiontreated with ethereal HCl
  7. customevaporated to dryness
  8. customThe resulting product was recrystallized from ethyl acetate and ether

Sources & evidence

ORD record
ord-f54e63fe817945f5aca1b6509ef67a57
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244888

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes