Dimethylamine, hydrochloride → HCID 66846346, compound

HRID 253157Notes

Reaction equation

HRID 253157 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[CH2:23][N:24]=[C:25]=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.Cl.CNC>ClCCl.O>[CH3:23][N:24]([CH3:25])[C:19](=[O:21])[CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 18763698HCID 18763698, compound

Product 1

HCID 66846346HCID 66846346, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution is prepared of 1.2 g (4.06 mmol) of 4-[2-(Boc-amino)ethoxy]benzeneacetic acid in 4 ml of dichloromethane and then 932 mg (4.87 mmol) of EDCI and 55 mg (0.406 mmol) of HOAT are added. After 10 minutes under agitation at ambient temperature, 400 mg (4.87 mmol) of dimethylamine hydrochloride are added. The reaction medium is then agitated at ambient temperature for 24 hours. The medium is then treated by the addition of 20 ml of water and then extracted 3 times with 50 ml of dichloromethane. The organic phases are then regrouped and washed 3 times with 50 ml of water, then dried on magnesium sulfate, and concentrated under reduced pressure. The raw product obtained is then purified by silica gel chromatography eluting with the help of a dichloromethane/ethanol mixture (95/5; v/v). In this way the expected product is obtained in the form of a colorless oil (yield=46%).

Workup

  1. extractionextracted 3 times with 50 ml of dichloromethane
  2. washwashed 3 times with 50 ml of water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe raw product obtained
  6. customis then purified by silica gel chromatography
  7. washeluting with the help of a dichloromethane/ethanol mixture (95/5; v/v)

Sources & evidence

ORD record
ord-5469e22eee0a4d49b8efb918e2f5e93b
Source dataset
uspto-grants-2011_01
Patent number
US07872021B2

Reaction notes

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