Dimethylamine → 1-(4-(Azetidin-3-yloxy)-2-chlorophenyl)-N,N-dimethylmethanamine

HRID 1035210Notes

Reaction equation

HRID 1035210 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]=1C)[CH3:3].N1CC(OC2C=CC(CN(C)C)=C(C)C=2)C1.CNC.[Cl:43]C1C=C(O)C=CC=1C=O>>[NH:12]1[CH2:13][CH:10]([O:9][C:8]2[CH:21]=[CH:22][C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[C:6]([Cl:43])[CH:7]=2)[CH2:11]1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 1853632-Chloro-4-hydroxybenzaldehydeHCID 58043102tert-Butyl 3-(4-((dimethylamino)methyl)-3-methylphenoxy)azetidine-1-carboxylateHCID 666563501-(4-(Azetidin-3-yloxy)-2-methylphenyl)-N,N-dimethylmethanamine

Product 1

HCID 666534891-(4-(Azetidin-3-yloxy)-2-chlorophenyl)-N,N-dimethylmethanamineYield 10%

Procedure

Using similar protocols as described in Examples 20A, 20B and 20C employing dimethylamine and 2-chloro-4-hydroxybenzaldehyde as starting material afforded 0.13 g (10%) of 47A as an oil. 1H NMR (500 MHz, CDCl3): δ 2.26 (s, 6H), 3.45 (s, 2H), 3.78 (m, 2H), 3.92 (m, 2H), 4.96 (m, 1H), 6.65 (d, 1H), 6.76 (d, 1H), 7.27 (m, 1H).

Sources & evidence

ORD record
ord-f01b130c04ae47c8a778dc50d8487c7a
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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