1-[3-(Dimethylamino)propyl]piperazine → Ammonia

HRID 469098

Reaction equation

HRID 469098 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][C:19]([C:21]([O:23]C)=O)=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.[CH3:26][N:27]([CH3:37])[CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C[Al](C)C>ClCCCl>[NH3:13].[CH3:37][N:27]([CH3:26])[CH2:28][CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][N:34]([C:21]([C:19]2[O:20][C:16]([CH2:15][N:13]([CH3:14])[S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:25])(=[O:12])=[O:11])=[N:17][N:18]=2)=[O:23])[CH2:35][CH2:36]1

Participants

6

Reactant 3

HCID 27362341-[3-(Dimethylamino)propyl]piperazineHCID 16682925TrimethylaluminumHCID 67217606Methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate

Product 2

HCID 222AmmoniaHCID 46176152N-{[5-({4-[3-(Dimethylamino)propyl]piperazin-1-yl}carbonyl)-1,3,4-oxadiazol-2-yl]methyl}-4-methoxy-N,2,6-trimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to general procedure AT using methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (30 mg, 0.08 mmol), N,N-dimethyl-3-(piperazin-1-yl)propan-1-amine (27 mg, 0.16 mmol) and trimethylaluminium (2 M in toluene, 0.08 mL) in DCE (5 mL). The crude product was purified using FCC, eluting with 95:4.5:0.5 DCM:MeOH:NH3, to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified
  3. washeluting with 95:4.5:0.5 DCM

Sources & evidence

ORD record
ord-f7b15319d22847419bcc366178068416
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Linked notes

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