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Acetic Anhydride → 1,2,3,4-Tetrahydro-2-[[1-(phenylmethyl)-4-piperidinyl]methylene]cyclopent[b]indol-1-one

HRID 22288
Notes
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Reaction equation

HRID 22288 reaction equation
[C:1]1(=[O:13])[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH2:3][CH2:2]1.[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([N-]C(C)C)(C)C.[Li+].C(OC(=O)C)(=O)C>C1COCC1>[C:15]1([CH2:14][N:21]2[CH2:26][CH2:25][CH:24]([CH:27]=[C:2]3[CH2:3][C:4]4[NH:5][C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=5[C:12]=4[C:1]3=[O:13])[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 895841-Benzylpiperidine-4-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 64246693,4-Dihydrocyclopenta(b)indol-1(2H)-one

Product 1

HCID 540822371,2,3,4-Tetrahydro-2-[[1-(phenylmethyl)-4-piperidinyl]methylene]cyclopent[b]indol-1-one

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of 1,2,3,4-tetrahydrocyclopent[b]-indol-1-one (440 mg, 2.6 mmol) and 1-benzylpiperidine-4-carboxaldehyde (581 mg, 2.86 mmol) in 90 ml dry THF was added 5.4 mmol of lithium diisopropylamide at -78° C. The mixture was stirred at -78° C. for 30 minutes, then warmed up to 0° C. for 1.5 hours, and then to r.t. for 15 minutes. Acetic anhydride (0.265 g, 2.6 mmol) was added, the mixture was stirred at r.t. for 1.5 hours and quenched ammonium chloride, water and extracted with chloroform. The organic layer was dried, concentrated, and purified through silica gel to give the title compound. 1HNMR (CDCl3)δ 1.45-1.7 (m, 3H), 1.8-2.3 (m, 4H), 2.8-3.0 (m, 2H), 3.46 (s, 2H), 3.55 (s, 2H), 6.5 (m, 1H), 7.1-7.4 (m, 8H), 7.9 (m, 1H), 9.2 (s, 1H) ppm.

Workup

  1. temperaturewarmed up to 0° C. for 1.5 hours
  2. waitto r.t. for 15 minutes
  3. stirringthe mixture was stirred at r.t. for 1.5 hours
  4. customquenched ammonium chloride, water
  5. extractionextracted with chloroform
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. custompurified through silica gel

Sources & evidence

ORD record
ord-38dbbafc6f744e7f8c4c06aaaa9e7d7c
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05428043

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes