1-Methylpiperazine → 1-(4-(Azetidin-3-yloxy)-2-chlorobenzyl)-4-methylpiperazine

HRID 1035212Notes

Reaction equation

HRID 1035212 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([CH2:35][N:36]([CH3:38])[CH3:37])=C(C)C=2)C1.CN1CCNCC1.[Cl:47]C1C=C(O)C=CC=1C=O>>[NH:12]1[CH2:11][CH:10]([O:9][C:8]2[CH:21]=[CH:22][C:5]([CH2:4][N:2]3[CH2:1][CH2:37][N:36]([CH3:38])[CH2:35][CH2:3]3)=[C:6]([Cl:47])[CH:7]=2)[CH2:13]1

Participants

5

Reactant 4

HCID 531671-MethylpiperazineHCID 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 666532661-(4-(Azetidin-3-yloxy)-2-chlorobenzyl)-4-methylpiperazineYield 32%

Procedure

Using similar protocols as described in Examples 20A, 20B and 20C employing 1-methylpiperazine and 2-chloro-4-hydroxybenzaldehyde as starting material afforded 0.32 g (32%) of 49A as an oil. 1H NMR (500 MHz, CDCl3): δ 2.29 (s, 3H), 2.3-2.7 (m, 8H), 3.55 (s, 2H), 3.78 (m, 2H), 3.92 (m, 2H), 4.96 (m, 1H), 6.64 (d, 1H), 6.74 (d, 1H), 7.31 (m, 1H), MS (APCI+) m/z 296 [M+H]+.

Sources & evidence

ORD record
ord-4469e6c2556b4ac6aa741cd08d6e19ac
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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