N,N-Dimethylglycine hydrochloride → 4-[4-(Dimethylaminoacetyl)-piperazin-1-yl]aniline

HRID 269808

Reaction equation

HRID 269808 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.Cl.[CH3:17][N:18]([CH3:23])[CH2:19][C:20](O)=[O:21].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN1CCCC1=O.C(N(CC)CC)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:20](=[O:21])[CH2:19][N:18]([CH3:23])[CH3:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 75605N,N-Dimethylglycine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 804471-(4-Nitrophenyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 230715454-[4-(Dimethylaminoacetyl)-piperazin-1-yl]aniline

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(4-nitrophenyl)piperazine and N,N-dimethylglycine hydrochloride were allowed to undergo the reaction using WSC hydrochloride and HOBt in 1-methyl-2-pyrrolidone in the presence of triethylamine. The resulting compound was subjected to-catalytic hydrogenation in the same manner as shown in Reference Example 3 to obtain 1-[4-(4-aminophenyl)piperazin-1-yl]-2-dimethylaminoethanone. NMR2: 2.30 (6H, s), 3.74-3.76 (4H, m), 6.64-6.68 (2H, m).

Sources & evidence

ORD record
ord-e95718d9ab524f7c8b6e020f9a0654ea
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Linked notes

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