Lithium Hydroxide → HCID 10119620, compound

HRID 892008

Reaction equation

HRID 892008 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][CH2:5][CH:6]([OH:23])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH2:10][CH2:9]1.[CH3:28][CH:29]1[CH2:35][C:34](=[O:36])[O:33][C:31](=[O:32])[CH2:30]1.[Li+].[OH-].C1COCC1.O>O>[Cl:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[Cl:21])[O:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:7][CH:6]([OH:23])[CH2:5][O:4][C:3]2[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=2[NH:1][C:34]([CH2:35][CH:29]([CH3:28])[CH2:30][C:31]([OH:33])=[O:32])=[O:36])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 778283-Methylglutaric anhydrideHCID 98699361-(2-Aminophenoxy)-3-[4-(3,4-dichlorophenoxy)-1-piperidinyl]-2-propanolHCID 21881883Oxolane--water (1/1)

Product 1

HCID 10119620HCID 10119620, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-aminophenoxy)-3-[4-(3,4-dichlorophenoxy)-1-piperidinyl]-2-propanol (75 uL, 0.2M/NMP) was mixed with 3-methyl glutaric anhydride (3 eq, 225 uL 0.2M /NMP) to get a product containing both esther and amide. After evaporation of the mixture it was treated with 3 eq 0.5M LiOH in (THF/water 1:4) for two hours at 80° C. to hydrolyse the esther. The reaction mixture was diluted with more water (2 mL) and the desired product was extracted with 5×500 uL EtOAc which was evaporated to dryness.

Workup

  1. customto get a product
  2. customAfter evaporation of the mixture it
  3. extractionthe desired product was extracted with 5×500 uL EtOAc which
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-5ec1299173da45a9b8e12c6aa3d84e9f
Source dataset
uspto-grants-2006_02
Patent number
US07005439B2

Linked notes

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