Hydrochloric Acid → HCID 67607204, compound

HRID 2280843Notes

Reaction equation

HRID 2280843 reaction equation
CO[C:3]1[C:30]([O:31][CH3:32])=[CH:29][C:6]2[C:7]([OH:28])=[CH:8][C:9]3[C:10]([CH3:27])([CH3:26])[C:11]4[CH:12]=[C:13]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[O:24][CH3:25])[CH:14]=[CH:15][C:16]=4[C:17]=3[C:5]=2[CH:4]=1.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C([Li])CCC.Cl>CCCCCC.O1CCCC1>[N:33]1([C:3]2[C:30]([O:31][CH3:32])=[CH:29][C:6]3[C:7]([OH:28])=[CH:8][C:9]4[C:10]([CH3:27])([CH3:26])[C:11]5[CH:12]=[C:13]([C:18]6[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=6[O:24][CH3:25])[CH:14]=[CH:15][C:16]=5[C:17]=4[C:5]=3[CH:4]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 67608446HCID 67608446, compoundHCID 178418339Butyllithium

Product 1

HCID 67607204HCID 67607204, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a 500 mL one-neck flask was added the product from Step 1(10 g), piperidine (5.2 mL and anhydrous tetrahydrofuran (150 mL). n-Butyl lithium in hexane solution (2.5M, 35 mL) was dropped to the mixture through addition funnel slowly. The reaction mixture was stirred at room temperature for 3 hours. The mixture was poured into cold aqueous hydrochloric acid (10%, 60 mL). The resulting mixture was extracted with ethyl acetate (200 mL) and the recovered top layer was filtered through a silica gel plug using ethyl acetate and hexane mixture as eluent. All silica gel plug and chromatography mentioned herein was carried out using ethyl acetate and hexanesmixture as eluent if not specified. Solid 2-(piperidin-1-yl)-3-methoxy-7,7-dimethyl-9-(2-methoxyphenyl)-7H-benzo[C]fluoren-5-ol (10 g) was obtained by re-crystallization from solution in ethyl acetate/hexanes.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (200 mL)
  2. filtrationthe recovered top layer was filtered through a silica gel plug

Sources & evidence

ORD record
ord-284097d7ef8d4f95b9335fee1aa8b245
Source dataset
uspto-grants-2015_09
Patent number
US09139552B2

Reaction notes

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