Hydrochloric Acid → HCID 86748388, compound

HRID 1769251Notes

Reaction equation

HRID 1769251 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]([C@H:7]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([I:21])[CH:15]=2)[CH2:12][C@H:11]2[N:22]([CH3:23])[C@@H:8]1[CH2:9][CH2:10]2)=[O:6].N([O-])=O.[Na+].[N-:28]=[N+:29]=[N-].[Na+].Cl>CC(O)=O.O>[ClH:1].[CH3:3][O:4][C:5]([C@H:7]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]=[N+:28]=[N-:29])=[C:16]([I:21])[CH:15]=2)[CH2:12][C@H:11]2[N:22]([CH3:23])[C@@H:8]1[CH2:9][CH2:10]2)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 86748390HCID 86748390, compound

Product 1

HCID 86748388HCID 86748388, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3β-[3'-iodo-4'-aminophenyl]tropan-2β-carboxylic acid methyl ester dihydrochloride (1a) (90 mg, 0.1902 mmol) in 1 mL of AcOH (3M) was added an aqueous solution of NaNO2 (17.3 mg, 0.2661 mmol, in 0.5 mL of H2O) at 0° C. After 30 min at this temperature NaN3 (19 mg, 0.2754 mmol) in 0.5 mL of H2O was added dropwise to the reaction mixture and stirred for 30 min at 0° C., then 30 min at room temperature. After removal of all solvent by evaporation, the residue was dissolved in CHCl3 and washed with H2O. The organic layer was dried over MgSO4 and concentrated to give an oil which was converted to HCl salt to yield 64 mg (72.7%) of 3β-[3'-iodo-4'-azidophenyl]tropan-2β-carboxylic acid methyl ester hydrochloride (1b) as a yellowish solid: mp 140°-143° C.; [α]25 -97.4° (c 0.115), MeOh); 1HNMR (250MHz, CDCl3) δ1.51-1.73 (m, 3) 2.07-2.16 (m, 2), 2.19 (s, 3, NCH3) 2.47 (m, 1), 2.80-2.93 (m, 2), 3.32 (m, 1, H-5), 3.51 (s, 3, OCH3), 3.54 (m, 1, H-1), 7.01 (d, 1, J-7.7, ArH), 7.28 (dd, 1, J=7.77, J=1, ArH), 7.60 (d, 1, J=1, ArH).

Workup

  1. custom30 min
  2. customat room temperature
  3. customAfter removal of all solvent
  4. customby evaporation
  5. dissolutionthe residue was dissolved in CHCl3
  6. washwashed with H2O
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated
  9. customto give an oil which

Sources & evidence

ORD record
ord-27a95967bf34448cb1b270ab49dfdd51
Source dataset
uspto-grants-1995_01
Patent number
US05380848

Reaction notes

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