Dimethylamine → Methyl 2-[(dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylate

HRID 2410486Notes

Reaction equation

HRID 2410486 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C[CH2:21][N:22](C(C)C)[CH:23](C)C.CS(Cl)(=O)=O.CNC.C1COCC1>C(Cl)Cl>[CH3:21][N:22]([CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[CH3:23]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66678471Methyl 2-(hydroxymethyl)-2'-methylbiphenyl-4-carboxylate

Product 1

HCID 66678469Methyl 2-[(dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylateYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(hydroxymethyl)-2′-methylbiphenyl-4-carboxylate (2.12 g, 8.27 mmol) in DCM (65 mL) was added DIEA (7.03 mL, 41.4 mmol) and methanesulfonyl chloride (768 μL, 9.93 mmol) at 0° C. and stirred for 25 min. After this time, a 2M solution of dimethylamine in THF (12.4 mL, 24.8 mmol) was added and the resulting mixture was stirred at RT for 16 hours. The reaction mixture was partitioned between DCM and a 5N aqueous solution of NaOH. The organic layer was dried (MgSO4) and concentrated under vacuum. A purification by chromatography (silica, DCM/MeOH) gave the title compound as a light yellow solid (2.03 g, 86%). 1H NMR (DMSO-d6) δ 8.27 (d, J=1.4 Hz, 1H), 7.95 (dd, J=7.8, 1.9 Hz, 1H), 7.32-7.18 (m, 4H), 7.06 (d, J=7.3 Hz, 1H), 3.94 (s, 3H), 3.24-3.10 (m, 2H), 2.11 (s, 6H), 2.01 (s, 3H). HPLC (Method A) Rt 2.90 min (Purity 100.0%). LC/MS (Method B): 284.1 (M−H)−.

Workup

  1. stirringthe resulting mixture was stirred at RT for 16 hours
  2. customThe reaction mixture was partitioned between DCM
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. customA purification by chromatography (silica, DCM/MeOH)

Sources & evidence

ORD record
ord-0a6b6639b64846e3af51ff5a3d71def8
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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