Hydrochloric Acid → HCID 68902946, compound

HRID 2110330Notes

Reaction equation

HRID 2110330 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([OH:32])[CH:16]([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:33].Cl.N1(C(C2C=CC=CC=2)C(O)CN2CCN(C)CC2)C2C(=CC=CC=2)C=C1.C(OC(N1CCNCC1)=O)(C)(C)C.Cl.O1CCOCC1>C(OCC)C>[ClH:33].[ClH:33].[N:23]1([CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]([OH:32])[CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 68904631HCID 68904631, compoundHCID 68906810HCID 68906810, compound

Product 1

HCID 68902946HCID 68902946, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In an analogous manner to EXAMPLE 1, step 3 (2SR,3RS)-4-(2-hydroxy-3-indol-1-yl-3-phenyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester was prepared from (2RS,3RS)-toluene-4-sulfonic acid 2-hydroxy-3-indol-1-yl-3-phenyl-propyl ester (EXAMPLE 1, step 3, 0.211 g, 0.5 mmol) and tert-butyl-1-piperazine carboxylate (0.19 g, 1.0 mmol). The product was dissolved in diethyl ether (3 mL) and treated with a 4N solution of hydrochloric acid in dioxane (0.75 mL, 3.0 mmol). The reaction mixture was then stirred at room temperature for 15 hours, and the crude solid product was filtered and recrystallized from ethanol with a minimum amount of diethyl ether to give the titled compound, (1RS,2SR)-1-(1H-indol-1-yl)-1-phenyl-3-piperazin-1-ylpropan-2-ol dihydrochloride as a tan solid. MS (ESI) m/z 336 ([M+H]+); HRMS: calcd for C21H25N30+H+, 336.20704; found (ESI, [M+H]+), 336.2085.

Workup

  1. filtrationthe crude solid product was filtered
  2. customrecrystallized from ethanol with a minimum amount of diethyl ether

Sources & evidence

ORD record
ord-ecfbab4dd01a45c7b4d664173ff713c4
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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