Dimethylformamide → HCID 68503779, compound

HRID 1176467Notes

Reaction equation

HRID 1176467 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:51]=[CH:50][CH:49]=[CH:48][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH:12]1[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]([C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[CH2:13]1)(O)=[O:2].C[N:53](C)[CH:54]=[O:55].C(Cl)(=O)C(Cl)=O>ClCCl>[OH:55][CH2:54][NH:53][C:1]([CH2:4][CH2:5][C:6]1[CH:51]=[CH:50][CH:49]=[CH:48][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH:12]1[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[CH:20][CH:19]=2)[CH2:16][CH2:15][N:14]([C:38]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39])[CH2:13]1)=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 68503104HCID 68503104, compound

Product 1

HCID 68503779HCID 68503779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.136 g of benzyl 3-{2-[2-(2-carboxyethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 3 ml of dichloromethane is admixed with 0.01 ml of N,N-dimethylformamide and 0.034 ml of oxalyl chloride and stirred at room temperature over 2 hours. The reaction mixture is concentrated by evaporation, and the residue is dissolved in 3 ml of tetrahydrofuran, cooled to 0° C. and added dropwise to the suspension of 0.033 g of N-methylhydroxylamine hydrochloride and 0.11 ml of triethylamine in a 4:1 tetrahydrofuran/water mixture (2 ml). The reaction mixture is stirred at room temperature over 14 hours, diluted with ethyl acetate, washed successively with 1N HCl, 1M aqueous sodium hydrogencarbonate solution and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.40 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.53.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. dissolutionthe residue is dissolved in 3 ml of tetrahydrofuran
  3. temperaturecooled to 0° C.
  4. additionadded dropwise to the suspension of 0.033 g of N-methylhydroxylamine hydrochloride and 0.11 ml of triethylamine in a 4:1 tetrahydrofuran/water mixture (2 ml)
  5. stirringThe reaction mixture is stirred at room temperature over 14 hours
  6. additiondiluted with ethyl acetate
  7. washwashed successively with 1N HCl, 1M aqueous sodium hydrogencarbonate solution and brine
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3846441702164f3b80914065b4c39c0b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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