Dimethylamine → HCID 66936465, compound

HRID 1366645Notes

Reaction equation

HRID 1366645 reaction equation
CS(O[C:6]1([CH2:23][CH3:24])[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[CH3:25][NH:26][CH3:27]>C(O)(C)C>[C:11]1([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:9][C:6]([CH2:23][CH3:24])([N:26]([CH3:27])[CH3:25])[CH2:7]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 19423696HCID 19423696, compound

Product 1

HCID 66936465HCID 66936465, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(diphenylmethyl)-3-ethyl-3-azetidinyl methanesulfonate (1.00 g, 2.89 mmol) (Ellsworth, Edmund Lee; Hoyer, Denton Wade; Hutchings, Kim Marie; Kendall, Jackie Diane; Murphy, Sean Timothy; Starr, Jeremy Tyson; Tran, Tuan Phong. WO 2005049605), dimethylamine (2 M in THF, 14.45 ml, 28.9 mmol) and TEA (0.80 ml, 5.78 mmol) in isopropanol was heated to 70° C. overnight. Standard work-up followed by RP-HPLC provided 1-(diphenylmethyl)-3-ethyl-N,N-dimethyl-3-azetidinamine (0.215 g, 25.3%). LCMS: (M+H)+ 295.2.

Sources & evidence

ORD record
ord-8f27dac665984ec0a72bdb35d7c55440
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…