1-(2-Methoxyphenyl)piperazine → HCID 9803240, compound

HRID 2306632Notes

Reaction equation

HRID 2306632 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]([O:17]NC=O)([CH3:16])([CH3:15])[CH3:14].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1.CN1CC[O:61][CH2:60]C1>CN(C)C=O.C(OCC)(=O)C>[C:13]([O:17][C:60](=[O:61])[NH:1][C@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:10]([N:54]1[CH2:55][CH2:56][N:51]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[O:44][CH3:43])[CH2:52][CH2:53]1)=[O:12])([CH3:14])([CH3:15])[CH3:16]

Participants

8

Reactant 5

HCID 13461-(2-Methoxyphenyl)piperazineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131724684HCID 131724684, compound

Product 1

HCID 9803240HCID 9803240, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of D-phenylalanine-N-t-butoxy-carboxamide (10.0 g, 37.7 mmol), 1-hydroxybenzotriazole (8.66 g, 64.1 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.20 g, 37.7 mmol) in dry dimethylformamide (50 mL) under a nitrogen atmosphere, was added 1-(2-methoxyphenyl)-piperazine (9.50 g, 41.5 mmol), followed by N-methylmorpholine (7.62 g, 75.4 mmol). The resulting mixture was stirred under nitrogen overnight, during which time it came up to room temperature. The reaction mixture was diluted with ethyl acetate and then washed with 0.1 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated sodium chloride solution. The combined organic layers dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the desired product (16.57 g, 99% yield) as a yellow oil which was pure enough to use without further purification: [α-D]25=−9.0 (c=1, MeOH); MS m/z=439 (M+).

Workup

  1. customcame up to room temperature
  2. washwashed with 0.1 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated sodium chloride solution
  3. dry with materialThe combined organic layers dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae42637df399441e8f1b299cdacf538e
Source dataset
uspto-grants-2004_12
Patent number
US06828324B2

Reaction notes

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