Hydrochloric Acid → 1-(4-(Azetidin-3-yloxy)-2-methylphenyl)-N,N-dimethylmethanamine

HRID 1035186Notes

Reaction equation

HRID 1035186 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][CH:10]2[CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)=[CH:7][C:6]=1[CH3:23])[CH3:3].Cl>CO>[NH:12]1[CH2:11][CH:10]([O:9][C:8]2[CH:21]=[CH:22][C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[C:6]([CH3:23])[CH:7]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58043102tert-Butyl 3-(4-((dimethylamino)methyl)-3-methylphenoxy)azetidine-1-carboxylate

Product 1

HCID 666563501-(4-(Azetidin-3-yloxy)-2-methylphenyl)-N,N-dimethylmethanamineYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Intermediate 20B (3.1 g, 9.7 mmol) was dissolved in MeOH (10 mL) and HCl in MeOH (1.25 M, 50 mL) was added. The reaction mixture was stirred at RT overnight. The mixture was concentrated, the residue was dissolved in water (15 mL) and DCM (100 mL) was added. While stirring an aqueous solution of K2CO3 (sat., 30 mL) was added and the two phases were separated through a phase separator. The solvent was removed by evaporation. There was obtained 1.96 g (92%) of 20C as a colorless oil. 1H NMR (600 MHz, CDCl3): δ 2.21 (s, 6H), 2.32 (s, 3H), 3.29 (s, 2H), 3.71-3.83 (m, 2H), 3.84-3.95 (m, 2H), 4.92-5.02 (m, 1H), 6.51 (d, 1H), 6.57 (s, 1H), 7.10 (d, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in water (15 mL)
  3. additionDCM (100 mL) was added
  4. stirringWhile stirring an aqueous solution of K2CO3 (sat., 30 mL)
  5. additionwas added
  6. customthe two phases were separated through a phase separator
  7. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2889bab4ebb64194a4b1c1cc43e84991
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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