Hydrochloric Acid → HCID 19380977, compound

HRID 258306Notes

Reaction equation

HRID 258306 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-c8417aeb0a214bfaa5aad4113cccd2c1
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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