Hydrochloric Acid → HCID 178486200, compound

HRID 1807998Notes

Reaction equation

HRID 1807998 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)=[O:4].[Li+].[OH-].[ClH:35]>O1CCOCC1.O>[Cl-:35].[C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C:18]([C@H:20]1[CH2:21][CH2:22][C@H:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])[CH:11]1[CH2:16][CH2:15][NH+:14]([CH3:17])[CH2:13][CH2:12]1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178499272HCID 178499272, compound

Product 1

HCID 178486200HCID 178486200, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 3-[(trans-4-methyl-cyclohexanecarbonyl)-(1-methyl-piperidin-4-yl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (176 mg, 0.387 mmol) and LiOH.monohydrate (48.8 mg, 1.16 mmol, 4.0 eq) in dioxane:water (3:1, 3.9 mL, 0.1 M) was heated at 50° C. for 5 h, cooled to room temp, acidified with aq. 1N HCl, concentrated, diluted with small amount of water and filtered off the product, and then dried (136 mg), which was triturated with hexanes several times to remove 4-methylcyclohexylacid furnished 4-[(2-carboxy-5-phenyl-thiophen-3-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-1-methyl-piperidinium chloride (Compound 11), 101 mg, 60% yield).

Workup

  1. concentrationconcentrated
  2. additiondiluted with small amount of water
  3. filtrationfiltered off the product
  4. customdried (136 mg), which
  5. customwas triturated with hexanes several times
  6. customto remove 4-methylcyclohexylacid

Sources & evidence

ORD record
ord-c881031d968a4a949c5e4da50afbf256
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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