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 1013290Notes

Reaction equation

HRID 1013290 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 1 NHCl (1 mL), and extracted with ethyl acetate. The organic phase was dried (Na2SO4) filtered, and concentrated. The concentrate was purified by reverse phase HPLC (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 phase HPLC (Zorbax SB-C18, 20-100% acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-23f391ebc9f740ac8514fe2e0769e2fb
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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