Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate → 1-(3-(1-Naphthyloxy)propyl)-3-piperidin-1-yl-1h-indole-2-carboxylic acid

HRID 533250Notes

Reaction equation

HRID 533250 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[C:16]2[C:30]([O:32]CC)=[O:31])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>[Li+].[OH-].CO.C1COCC1>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[C:16]2[C:30]([OH:32])=[O:31])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 67316989Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate

Product 1

HCID 251019521-(3-(1-Naphthyloxy)propyl)-3-piperidin-1-yl-1h-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 86635511LiOH methanol THFSolvent

Procedure

A mixture of EXAMPLE 74A (30 mg) in 1N aqueous LiOH/methanol/THF (1 mL/1 mL/1 mL) was stirred at room temperature overnight. The reaction mixture was acidified with 1NHCl (1 mL), and extracted with ethyl acetate. The organic phase was dried (Na2SO4) filtered, and concentrated. The concentrate was purified by reverse phaseHPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid). 1H NMR (400 MHz, DMSO-d6) δ 16.82 (s, 1H), 8.08 (d, 1H), 7.96 (d, 1H), 7.85 (d, 1H), 7.69 (d, 1H), 7.48 (m, 3H), 7.36 (t, 1H), 7.24 (m, 1H), 7.13 (t, 1H), 6.83 (t, 1H), 4.89 (t, 2H), 4.16 (t, 2H), 3.24 (br, 4H), 2.33 (m, 2H), 1.70 (br, 6H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by reverse phaseHPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4584a8b7e4634a3bad0e561930278bd2
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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