Acetic Anhydride → HCID 54082237, compound

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

Participants

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

temperaturewarmed up to 0° C. for 1.5 hours
waitto r.t. for 15 minutes
stirringthe mixture was stirred at r.t. for 1.5 hours
customquenched ammonium chloride, water
extractionextracted with chloroform
customThe organic layer was dried
concentrationconcentrated
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

Linked notes

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