Hydrochloric Acid → HCID 68576648, compound

HRID 639521Notes

Reaction equation

HRID 639521 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(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[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]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[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 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68576861HCID 68576861, compound

Product 1

HCID 68576648HCID 68576648, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-(3-chloropropyloxy)morphinan.HCl 54 (3 mg, 0.008 mmol) in dry DMF (0.15 mL) was added potassium carbonate (7 mg, 0.024 mmol), benzylbromide (2 μL, 0.032 mmol) sequentially and the mixture was stirred at 50° C. After starting material disappeared on TLC, solvent was concentrated and column chromatography gave 3 mg (87%) of the title compound: 1H NMR (300 MHz, CDCl3) δ7.15˜7.35 (5H, m); 7.05 (1H, d); 6.80 (1H, s); 6.73 (1H, d); 4.10 (2H, t); 3.55˜3.85 (4H, m); 3.05 (1H, m); 2.80 (1H, m); 2.56 (1H, m); 2.40 (1H, m); 2.00˜2.30 (4H, m); 1.00˜1.90 (10H, m).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-89b3ee0a80f941c7b1f5dc256d30bc19
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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