Benzylethanolamine → 1-Benzyl-4-(2-methylphenyl)piperazine-2-carboxamide

HRID 128578Notes

Reaction equation

HRID 128578 reaction equation
C(NCCO)C1C=CC=CC=1.Cl.ClCCNCC1C=CC=CC=1.S(Cl)(Cl)=O.Cl.[CH2:29]([NH:36][CH2:37][CH2:38][NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH3:46])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.NC1C(C)=CC=CC=1.Br[CH:56]([CH2:60]Br)[C:57]([NH2:59])=[O:58]>>[CH2:29]([N:36]1[CH2:37][CH2:38][N:39]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH3:46])[CH2:60][CH:56]1[C:57]([NH2:59])=[O:58])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 6

HCID 4348BenzylethanolamineHCID 7242O-ToluidineHCID 24386Thionyl ChlorideHCID 857982,3-DibromopropionamideHCID 13054189Benzenemethanamine, N-(2-chloroethyl)-, hydrochloride (1:1)2×HCID 21837245N-benzyl-N'-(2-methylphenyl)-1,2-diaminoethane hydrochloride2×

Product 1

HCID 218372261-Benzyl-4-(2-methylphenyl)piperazine-2-carboxamide

Procedure

2-Benzylaminoethanol (18.8 ml, 20 g, 0.13 mol) was converted to N-(2-chloroethyl)-N-benzylamine hydrochloride with thionyl chloride (19 ml, 31 g, 0.26 mol) according to the procedure described in J. Chem. Soc. 1955, 896. N-(2-chloroethyl)-N-benzylamine hydrochloride (4.0 g, 19 mmol) was converted to N-benzyl-N'-(2-methylphenyl)-1,2-diaminoethane hydrochloride by the procedure of Syn. Comm. 18, 45-50 (1988), using o-toluidine (6.1 ml, 6.1 g, 57 mmol) in place of aniline. 1-benzyl-4-(2-methylphenyl)piperazine-2-carboxamide was prepared from 2,3-dibromopropionamide (7.9 g, 34 mmol) by the procedure of J. Med. Chem. 35, 743-750 (1992) using N-benzyl-N'-(2-methylphenyl)-1,2-diaminoethane hydrochloride (4.95 g, 18 mmol) in place of N-benzyl-N'-phenyl-1,2-diaminoethane hydrochloride.

Sources & evidence

ORD record
ord-12a917706c3a42e59b8d4c7e46de77c9
Source dataset
uspto-grants-1995_11
Patent number
US05464788

Reaction notes

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