1,2-Dichloroethane → 2-{4-[2-amino-3-(4-fluorophenyl)-propionyl]-3-methoxymethyl-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide HCl

HRID 720204Notes

Reaction equation

HRID 720204 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:29](=[O:32])[NH:30][CH3:31])[CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[CH2:13][CH:12]1[CH2:33][O:34][CH3:35])=[O:10])(C)(C)C.[Cl:45]CCCl>Cl.O1CCOCC1>[ClH:45].[NH2:7][CH:8]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]([CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[C:29]([NH:30][CH3:31])=[O:32])[CH2:13][CH:12]1[CH2:33][O:34][CH3:35])=[O:10]

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 69587995{1-(4-Fluoro-benzyl)2-[2-methoxymethyl-4-(1-methylcarbamoyl-2-naphthalen-2-yl-ethyl)-piperazin-1-yl]-2oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 695877352-{4-[2-amino-3-(4-fluorophenyl)-propionyl]-3-methoxymethyl-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propionamide HClYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

{1-(4-Fluoro-benzyl)2-[2-methoxymethyl-4-(1-methylcarbamoyl-2-naphthalen-2-yl-ethyl)-piperazin-1-yl]-2oxo-ethyl}-carbamic acid tert-butyl ester, 65, is dissolved in 4M HCl in dioxane (60 mL). The reaction mixture is stirred for 90 minutes then 1,2-dichloroethane (60 mL) is added. The solution is concentrated in vacuo to afford 3.6 g (98% yield) of the desired product.

Workup

  1. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-18736ad6c1ff46a69dbc04d41b9953e5
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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