Triethylamine → HCID 21887383, compound

HRID 722972Notes

Reaction equation

HRID 722972 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].Cl.Cl.[NH2:8][C:9]1[CH:10]=[C:11]([C:17](=[O:38])[CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH2:36][CH3:37])[CH2:22][CH2:21]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].C(N(CC)CC)C>O1CCCC1>[ClH:5].[CH2:36]([O:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[O:28][CH2:27][CH2:26][N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][CH2:18][C:17]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([NH:8][S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=2)=[O:38])[CH2:21][CH2:22]1)[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21887766HCID 21887766, compound

Product 1

HCID 21887383HCID 21887383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (0.108 ml) was added to a solution of 1-(3-amino-4-methoxyphenyl)-3-{1-[2-(2-ethoxyphenoxy)ethyl]-4-piperidinyl}-1-propanone dihydrochloride (300 mg) obtained in Example 327 and triethylamine (0.195 ml) in tetrahydrofuran (10 ml) at room temperature, the mixture was stirred for 12 hours, and the reaction mixture was concentrated under reduced pressure. Water (30 ml) and ethyl acetate (40 ml) were added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1)) to give a free base compound of the title compound as a colorless oil (291 mg). The free base compound (290 mg) was treated with a hydrogen chloride-ethanol solution to give the title compound (277 mg) as colorless amorphous powders.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater (30 ml) and ethyl acetate (40 ml) were added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1))

Sources & evidence

ORD record
ord-1dfa5d24dcdc40f9a7b68f92ce2c9829
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

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