Water → HCID 19381064, compound

HRID 258291Notes

Reaction equation

HRID 258291 reaction equation
[H-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].[Cl:7][C:8]12C[CH:9]1[C:10]1[C:19]([CH:20]=[CH:21]2)=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:33])[CH2:31]Br)[CH2:25][CH2:24]1.O.[CH3:36]N(C)C=O>F[B-](F)(F)F.[Ag+].C(Cl)Cl>[Cl:7][C:8]1[CH:21]=[CH:20][C:19]2[CH:18]3[CH2:36][C:11]([CH2:22][N:23]4[CH2:24][CH2:25][CH:26]([NH:29][C:30](=[O:33])[CH2:31][O:6][CH:3]([CH3:5])[CH3:4])[CH2:27][CH2:28]4)([C:12]4[C:17]3=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:10]=2[CH:9]=1

Participants

8

Reactant 5

HCID 962WaterHCID 3776IsopropanolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 67753309HCID 67753309, compound

Product 1

HCID 19381064HCID 19381064, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled (ice bath) stirred suspension of 97% sodium hydride (180 mg, 7.5 mmol) in N,N-dimethylformamide (3 mL) was added isopropanol (0.58 mL, 7.5 mmol). After stirring for 0.5 h at 0° C., the reaction was added 2-chloro-9-[4-(bromoacetamido)piperidinomethyl]methanoanthracene (575 mg, 1.25 mmol) and silver tetrafluoroborate (243 mg, 1.25 mmol). The reaction was allowed to warm to ambient temperature and stirred for an additional 18 h. The mixture was treated with water (50 mL) and methylene chloride (100 mL) and filtered through celite with methylene chloride (3×50 mL) washes. After separating the aqueous layer from the filtrate, the organic layer was washed with brine (50 mL), dried (sodium sulfate), filtered, and concentrated to give a yellow syrup. Chromatography of this material over silica gel (eluant: 9:1 methylene chloride/ether) gave the title compound as a light yellow glass (265 mg, 48%), mp 50.0°-3.0° C.; MS(CI): 439 (M+H); NMR (300 MHz,DMSO-d6): 1.10(d, 6H, J=6.0 Hz), 1.51-1.61(br m, 4H), 2.26(br m, 2H), 2.47(m, 2H), 2.93(br m, 2H), 3.29(d, part.submerged by H2O, 1H), 3.38(d, 1H, J=14.1 Hz), 3.57(septet, 1H, J=6.2 Hz), 3.62(br m, 1H), 3.78(s, 1H), 4.34(s, 1H), 6.96(br m, 3H), 7.20(br d, 2H, J=8.9 Hz), 7.27(d, 2H, J=7.7 Hz), 7.34(d, 1H, J=8.0 Hz).

Workup

  1. temperatureTo a cooled (ice bath)
  2. stirringAfter stirring for 0.5 h at 0° C.
  3. stirringstirred for an additional 18 h
  4. filtrationfiltered through celite with methylene chloride (3×50 mL) washes
  5. customAfter separating the aqueous layer from the filtrate
  6. washthe organic layer was washed with brine (50 mL)
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a yellow syrup

Sources & evidence

ORD record
ord-0311ddb6b0fc40deb65535c8843c06b1
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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