Hydrochloric Acid → HCID 15637642, compound

HRID 742557Notes

Reaction equation

HRID 742557 reaction equation
Cl.Cl.Cl.[OH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH:6]1[N:11]1[CH2:16][CH2:15][C:14]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].[I:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Cl)=[CH:35][CH:34]=1>C(O)C>[I:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][N:8]2[CH2:9][CH2:10][CH:5]([OH:4])[CH:6]([N:11]3[CH2:16][CH2:15][C:14]4([C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH2:19][CH2:18][CH2:17]4)[CH2:13][CH2:12]3)[CH2:7]2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 8172111-(Chloromethyl)-4-iodobenzeneHCID 19426302HCID 19426302, compound

Product 1

HCID 15637642HCID 15637642, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the hydrochloride of 21c (250 mg, 0.67 mmol), potassium carbonate (463 mg, 3.35 mmol) and 4-iodobenzyl chloride (298 mg, 1.00 mmol) in absolute ethanol (25 mL) was refluxed for 16 h. When the mixture had cooled, salts were filtered off and the volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate (25 mL) and the solution was successively washed with water (25 mL) and brine (25 mL). The organic layer was then dried (Na2SO4) and concentrated. The product was purified by chromatography (silica gel, hexanes/ethyl acetate: 50/50) and (13e) was obtained as a colorless oil (226 mg, 52%). The hydrochloride was prepared in a satd HCl/ether soln and recrystallized twice from 50% isopropyl alcohol-hexanes to yield a yellow powder; mp 256.3° C.; 1H NMR (CDCl3) δ1.56-2.18 (2 m, 8, 2 N--C H2 --C H2), 2.40-2.45 (d, 2H, Ar--C H2 --CH2, J=10.1 Hz), 2.51-2.60 (m, 2, C H2 --CHOH), 2.72-2.78 (m, 4, Ar--CH2 -C H2 --C H2), 2.84-2.97 (t, 2, N--C H2 --CH2 --CHOH, J=11.9 Hz), 3.05-3.50 (d, 2, CHN--C H2 --N, J=10.4 Hz), 3.40-3.55 (m, 4, C H--OH+Ar--CH2 --N+CHN), 3.81 (s, 1, OH), 7.22-7.02 (m, 4, arom.), 7.42-7.46 (d, 2, arom., J=7.7 Hz), 7.63-7.67 (d, 2, arom., J=8.2 Hz).

Workup

  1. temperaturewas refluxed for 16 h
  2. temperatureWhen the mixture had cooled
  3. filtrationsalts were filtered off
  4. customthe volatiles were removed under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  6. washthe solution was successively washed with water (25 mL) and brine (25 mL)
  7. dry with materialThe organic layer was then dried (Na2SO4)
  8. concentrationconcentrated
  9. customThe product was purified by chromatography (silica gel, hexanes/ethyl acetate: 50/50)

Sources & evidence

ORD record
ord-d8650fc70e8d4175a94c5d61ba044ead
Source dataset
uspto-grants-1996_09
Patent number
US05554752

Reaction notes

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