Hydrochloric Acid → HCID 19380977, compound

HRID 2209601Notes

Reaction equation

HRID 2209601 reaction equation
[CH:1]1[C:14]2[C:13]3([C:16]([N:18]4[CH2:23][CH2:22][CH:21]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)[CH2:20][CH2:19]4)=O)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.B.O1CCCC1.[ClH:36]>O1CCCC1>[ClH:36].[ClH:36].[CH:11]1[C:12]2[C:13]3([CH2:16][N:18]4[CH2:23][CH2:22][CH:21]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)[CH2:20][CH2:19]4)[CH2:15][CH:6]([C:5]4[C:14]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 19380970HCID 19380970, compound

Product 1

HCID 19380977HCID 19380977, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cooled solution of 1-(9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)-4-(4-morpholinyl)piperidine (2.29 g, 5.89 mmol) in tetrahydrofuran (35 mL) was added 1M borane-tetrahydrofuran in tetrahydrofuran (17,7 mL, 17.7 mmol). The reaction was refluxed for 5 h and then was cooled with an ice bath. This mixture was added dropwise a solution of methanolic hydrochloride (25 mL). The ice bath was removed and the solution was refluxed for 0.5 h. The resulting precipitate was filtered with hexane wash (50 mL). The solid was recrystallized from acetonitrile to give the title compound as a white solid (1.62 g, 68%), mp 257.0°-259.0° C.; MS(CI): 375 (M+H); NMR (250 MHz,DMSO-d6): 2.27(m, 6H), 2.75(s, 2H), 3.11(br s, 2H), 3.40(br s, 2H), 3.66(m, 2H), 3.94(m, 4H), 4.38(m, 3H), 4.47(s, 1 H), 7.00(m, 4H), 7.34(m, 4H), 10.46(br s, 1H), 11.91(br s, 1H).

Workup

  1. temperatureThe reaction was refluxed for 5 h
  2. temperaturewas cooled with an ice bath
  3. customThe ice bath was removed
  4. temperaturethe solution was refluxed for 0.5 h
  5. filtrationThe resulting precipitate was filtered with hexane
  6. washwash (50 mL)
  7. customThe solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-50406472f8dc47a0abfab2471060e1d7
Source dataset
uspto-grants-1995_10
Patent number
US05455246

Reaction notes

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