Phosphoric Acid → (s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine phosphate

HRID 429836Notes

Reaction equation

HRID 429836 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[P:27](=[O:31])([OH:30])([OH:29])[OH:28]>C(O)C>[P:27]([OH:31])([OH:30])([OH:29])=[O:28].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([S:23]([CH3:26])(=[O:24])=[O:25])[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 10927016(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine

Product 1

HCID 20706302(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine phosphateYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-N-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine (0.4 grams, 1.05 mmole) was dissolved in (10 ml) hot 10% aqueous ethanol. To this solution was added 85% phosphoric acid (0.122 grams, 1.06 mmole). The solution was stored at 22° C. for 16 hours. The deposited crystals were collected and dried in vacuo at 70° C. to give (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine phosphate (0.454 grams, 97%), m.p. 209-210° C.

Workup

  1. customThe deposited crystals were collected
  2. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-cf4c8edd270c42679adaad821c91caa7
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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