Hydrochloric Acid → HCID 67171136, compound

HRID 2280846Notes

Reaction equation

HRID 2280846 reaction equation
N1(C2C=CC(C(C3C=CC=CC=3)=O)=CC=2)CCNCC1.CO[C:23]1[C:42]([O:43][CH3:44])=[CH:41][C:26]2[C:27]([OH:40])=[CH:28][C:29]3[C:30]([CH3:39])([CH3:38])[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=4[C:37]=3[C:25]=2[CH:24]=1.[NH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1.C([Li])CCC.Cl>CCCCCC.O1CCCC1>[N:45]1([C:23]2[C:42]([O:43][CH3:44])=[CH:41][C:26]3[C:27]([OH:40])=[CH:28][C:29]4[C:30]([CH3:38])([CH3:39])[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=5[C:37]=4[C:25]=3[CH:24]=2)[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 1519739HCID 1519739, compoundHCID 21696414HCID 21696414, compoundHCID 178418339Butyllithium

Product 1

HCID 67171136HCID 67171136, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To an oven-dried 500 mL one-neck flask was added the product of Step 3, Example 1, of U.S. Pat. No. 6,296,785B1, 2,3-dimethoxy-7,7-dimethyl-7H-benzo[C]fluoren-5-ol (10 g) which is included herein as reference, piperidine (5.2 mL) and anhydrous tetrahydrofuran (150 mL). n-Butyl lithium in hexane solution (2.5M, 35 mL) was dropped to the mixture 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 mixture was extracted with ethyl acetate (200 mL) and the recovered top layer was filtered through a silica gel plug. The desired product 2-piperidino-3-methoxy-7,7-dimethyl-7H-benzo[C]fluoren-5-ol (10 g) was obtained by recrystallization from solution in ethyl acetate/hexanes.

Workup

  1. extractionThe 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-0abb82f0bacf48bdbb8f693c05982bf5
Source dataset
uspto-grants-2015_09
Patent number
US09139552B2

Reaction notes

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