Methyl Bromide → HCID 9953901, compound

HRID 2116873Notes

Reaction equation

HRID 2116873 reaction equation
[CH3:1][Br:2].[CH:3]([N:6]([CH:24]([CH3:26])[CH3:25])[CH2:7][CH2:8][C@@H:9]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[OH:23])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])[CH3:4]>CC(C)=O>[Br-:2].[OH:23][C:17]1[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:8][CH2:7][N+:6]([CH:3]([CH3:5])[CH3:4])([CH:24]([CH3:26])[CH3:25])[CH3:1]

Participants

4

Reactant 2

HCID 6323Methyl BromideHCID 443879Tolterodine

Product 1

HCID 9953901HCID 9953901, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
22.5 °C

Procedure

A sealed mixture of methyl bromide (100 g) and 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-methylphenol (14 g) in acetone (100 ml) is stirred at 20-25° C. for 4 days. The mixture is cooled to −10° C. and the precipitate is filtered off and washed with ether and dried to give the title compound, mp 189-191° C. (dec). Anal Calcd for C23H34BrNO: C, 65.71; H, 8.15; Br, 19.00; N, 3.33. Found: C, 65.61; H, 8.34; Br, 19.12; N, 3.32. [α]D (c=1, MeOH) +25° C. 1H NMR [(CD3)2SO] δ 1.25, 2.18, 2.48, 2.81, 3.05, 3.89, 4.22, 6.70, 6.83, 7.08, 7.19, 7.33, and 9.3.

Workup

  1. temperatureThe mixture is cooled to −10° C.
  2. filtrationthe precipitate is filtered off
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-5dfc899a0dc34adcbc5c86a4053b9210
Source dataset
uspto-grants-2008_10
Patent number
US07439397B2

Reaction notes

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