Hydrochloric Acid → HCID 68576804, compound

HRID 639519Notes

Reaction equation

HRID 639519 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][C@H:11]3[NH:22][CH2:21][CH2:20][C@@:17]4([C:18]=2[CH:19]=1)[C@H:12]3[CH2:13][CH2:14][CH2:15][CH2:16]4.Cl.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][C@H:11]3[N:22]([S:32]([CH3:31])(=[O:34])=[O:33])[CH2:21][CH2:20][C@@:17]4([C:18]=2[CH:19]=1)[C@H:12]3[CH2:13][CH2:14][CH2:15][CH2:16]4

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68576861HCID 68576861, compound

Product 1

HCID 68576804HCID 68576804, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(3-chloropropyloxy)morphinan.HCl 54 (3 mg, 0.008 mmol) and triethylamine (7 μL, 0.050 mmol) in dry dichloromethane (0.3 mL) was added methanesulfonylchloride (2 μL, 0.025 mmol) and the mixture was stirred at room temperature. After starting material disappeared on TLC, solvent was removed and column chromatography gave 3 mg (88%) of title compound: 1H NMR (300 MHz, CDCl3) δ7.01 (1H, m); 6.85 (1H, d); 6.70 (1H, d.d); 4.05 (3H, m); 3.78 (2H, t); 3.56 (1H, d.d.); 3.15 (1H, d.d.); 2.90 (3H, s); 2.83 (2H, m); 2.32 (1H, m); 2.20 (2H, m); 1.00˜1.90 (10H, m).

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-f59fb1ab045045c7b1418cca19092eca
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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