Hydrochloric Acid → HCID 18184522, compound

HRID 1358461Notes

Reaction equation

HRID 1358461 reaction equation
C(O)(=O)C(O)=O.C([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]([CH2:30][C:31]1[CH:36]=[C:35]([Br:37])[C:34]([O:38][CH3:39])=[C:33]([Br:40])[CH:32]=1)[NH:20][CH2:19][CH2:18]2)C1C=CC=CC=1.[ClH:41]>CO>[ClH:41].[Br:40][C:33]1[CH:32]=[C:31]([CH:36]=[C:35]([Br:37])[C:34]=1[O:38][CH3:39])[CH2:30][CH:21]1[C:22]2[C:17](=[CH:16][C:15]([OH:14])=[C:24]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=2)[CH2:18][CH2:19][NH:20]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18184510HCID 18184510, compound

Product 1

HCID 18184522HCID 18184522, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[6-benzyloxy-1-(3,5-dibromo-4-methoxy-benzyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-methanesulfonamide oxalate (3.98 g, 0.0057 mol) in a mixture of conc. HCl (50 mL) and methanol (50 mL) was refluxed for 1h, cooled and concentrated. A residue was crystallized from methanol—ethyl ether mixture. Yield 2.75 g (87%), M.p. 244-245° C. (dec.). 1H NMR (300 MHz, DMSO) δ 2.9 (s, 3H), 2.95-3.22 (m, 4H), 3.25-3.45 (m, 2H), 3.79 (s, 3H), 4.67 (m, 1H), 6.75 (s, 1H), 7.15 (s, 1H), 7.79 (s, 2H), 8.84 (s, 1H), 9.26 (d, J=12.6 Hz, 2H), 10.18 (s, 1H). Anal. (C18H21Br2ClN2O4S) calcd., C 38.83, H 3.80, N 5.03; found C 38.91, N 4.83.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customA residue was crystallized from methanol—ethyl ether mixture

Sources & evidence

ORD record
ord-6fc011ac48ad4e8da8c3a45b3e8241e7
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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