Hydrochloric Acid → HCID 68576837, compound

HRID 639516Notes

Reaction equation

HRID 639516 reaction equation
[C:1]1([NH:7][C:8]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:15][C@H:16]4[NH:27][CH2:26][CH2:25][C@@:22]5([C:23]=3[CH:24]=2)[C@H:17]4[CH2:18][CH2:19][CH2:20][CH2:21]5)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH2:37][CH2:38][Cl:39]>CN(C=O)C>[C:1]1([NH:7][C:8]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:15][C@H:16]4[N:27]([CH2:36][CH2:37][CH2:38][Cl:39])[CH2:26][CH2:25][C@@:22]5([C:23]=3[CH:24]=2)[C@H:17]4[CH2:18][CH2:19][CH2:20][CH2:21]5)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 68576671HCID 68576671, compound

Product 1

HCID 68576837HCID 68576837, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-phenylcarbamoyloxymorphinan.HCl 30 (2.8 mg, 0.007 mmol) in dry DMF (0.15 mL) was added potassium carbonate (5.4 mg, 0.021 mmol), 1-bromo-3-chloropropane (1.9 μL, 0.042 mmol) sequentially and the mixture was stirred at 50° C. After starting material disappeared on TLC, solvent was concentrated and column chromatography gave 2.1 mg (70%) of the title compound: 1H NMR (300 MHz, CDCl3) δ7.35 (4H, m); 7.10 (2H, m); 6.85 (1H, d); 6.75 (1H, d.d.); 6.28 (1H, s); 4.38 (1H, m); 4.10 (2H, t); 3.80 (2H, t); 3.65 (1H, m); 3.14 (1H, d.d.); 2.83 (2H, m); 2.37 (1H, m); 2.25 (2H, m); 1.00˜1.80 (10H, m).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-e9c839ceb2b7425a8f338dee58f95e4d
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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