Methanesulfonic Acid → 7-(2-(methyloxy)-6-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine methanesulfonate

HRID 63283Notes

Reaction equation

HRID 63283 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=2)[C:4]=1[C:18]1[CH:28]=[CH:27][C:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=2[CH:19]=1.[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>CC(O)C>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=2)[C:4]=1[C:18]1[CH:28]=[CH:27][C:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=2[CH:19]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 601940981398695-47-0

Product 1

HCID 601965357-(2-(methyloxy)-6-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine methanesulfonateYield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

7-(2-(methyloxy)-6-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (300.0 mg; 1.0 eq) was weighed into a 20-mL vial containing a stir bar and combined with 2-propanol (6.0 mL). The suspension was heated to 40° C. and stirred for 15 min (solids dissolved). Seeds of the methanesulfonate salt were added (˜1 mg). Methanesulfonic acid (3M in water; 1.1 eq.; 293.0 uL in aliquots: 43, 50, 100, and 100 μL) was added. White solid precipitated after the first aliquot (43 μL). The suspension was re-seeded with the methansulfonate salt (˜1 mg). After all aliquots of the counterion solution were added, the suspension was stirred at 40° C. for 1 hr. The suspension was cooled to 5° C. at 0.5° C./min and stirred for 15 min. The product was isolated on a Büchner funnel using #1 Whatman filter paper, air-dried for 30 min, and dried at 40° C. under vacuum for 12 hrs. The title compound was produced as a white crystalline powder. A yield of 82% was obtained.

Workup

  1. additionvial containing a stir bar
  2. dissolution(solids dissolved)
  3. customWhite solid precipitated after the first aliquot (43 μL)
  4. additionAfter all aliquots of the counterion solution were added
  5. stirringthe suspension was stirred at 40° C. for 1 hr
  6. temperatureThe suspension was cooled to 5° C. at 0.5° C./min
  7. stirringstirred for 15 min
  8. customThe product was isolated on a Büchner funnel
  9. filtrationfilter paper
  10. customair-dried for 30 min
  11. customdried at 40° C. under vacuum for 12 hrs

Sources & evidence

ORD record
ord-df01f1cd56f248728063c2c3711b609b
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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