4-Methylmorpholine → N-[[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]carbonyl]-DL-serine methyl ester

HRID 2043731Notes

Reaction equation

HRID 2043731 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]1)=[O:11].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.Cl.[CH3:41][O:42][C:43](=[O:48])[CH:44]([CH2:46][OH:47])[NH2:45]>ClCCl>[CH3:41][O:42][C:43](=[O:48])[CH:44]([CH2:46][OH:47])[NH:45][C:18]([CH:15]1[CH2:14][CH2:13][N:12]([C:10](=[O:11])[CH2:9][C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:17][CH2:16]1)=[O:20]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 517373Methyl DL-serinate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 625380021-[(2,5-Dimethylphenyl)acetyl]-4-piperidinecarboxylic acid2×

Product 1

HCID 67461522N-[[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]carbonyl]-DL-serine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[(2,5-dimethylphenyl)acetyl]-4-piperidinecarboxylic acid (i.e. the product of Example 9, Step B) (1.44 g, 5.23 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.1 g, 5.75 mmol), and N-methylmorpholine (529 mg, 5.23 mmol) in 5 mL of dichloromethane was stirred at room temperature for 15 minutes. DL-Serine methyl ester hydrochloride (814 mg, 5.23 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction was partitioned between 1 N aqueous hydrochloric acid (10 mL) and dichloromethane (10 mL), and the organic layer was washed with 1 N aqueous hydrochloric acid, water and brine, dried over MgSO4 and concentrated under reduced pressure to give 1.61 g of the title compound.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 h
  2. customThe reaction was partitioned between 1 N aqueous hydrochloric acid (10 mL) and dichloromethane (10 mL)
  3. washthe organic layer was washed with 1 N aqueous hydrochloric acid, water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1957aede7c14c9abba05e8f32af8d25
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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