Hydrochloric Acid → HCID 68576776, compound

HRID 639520Notes

Reaction equation

HRID 639520 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.[C:31](Cl)(=[O:33])[CH3:32]>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]([C:31](=[O:33])[CH3:32])[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 6367Acetyl chlorideHCID 8471TriethylamineHCID 68576861HCID 68576861, compound

Product 1

HCID 68576776HCID 68576776, compoundYield 82%

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 acetyl chloride (1.8 μL, 0.025 mmol) and the mixture was stirred at room temperature. After starting material disappeared on TLC, solvent was concentrated and column chromatography gave 2.5 mg (82%) of the title compound: 1H NMR (300 MHz, CDCl3) δ6.96 (1H, t); 6.83 (1H, d); 6.75 (1H, d. d.); 4.92 (1H, m); 4.15 (2H, t); 3.81 (2H, t); 3.75 (1H, m); 3.12 (1H, m); 2.95 (1H, m); 2.62 (1H, m); 2.30 (1H, m); 2.18 (2H, m); 2.05 (3H, s); 1.00˜1.80 (10H, m).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-d9ca420c17c2468ea77da431bccc112d
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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