Hydrochloric Acid → HCID 69739228, compound

HRID 966525Notes

Reaction equation

HRID 966525 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:28]>C(Cl)Cl.C(OCC)C>[ClH:28].[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10109292HCID 10109292, compound

Product 1

HCID 69739228HCID 69739228, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-5-(2-pyrrolidin-1-yl-ethyl)-1H-indole-3-carboxylic acid benzyl ester (70 mg, 0.19 mmol) in methylene chloride (1 mL) was added hydrogen chloride in diethyl ether. The resulting mixture was concentrated in vacuo and triturated with diethyl ether to give 61 mg (79%) of titled compound as a white foam: mp 76-78° C.; Anal. Calcd for C23H27Cl1N2O2.2.9H2O: C, 61.23; H, 7.33; N, 6.21. Found: C, 60.83; H, 6.93; N, 5.92.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-87b097b3a21d46bfa01007a5fe3601ab
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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