Hydrochloric Acid → 8-(2-Chlorophenyl)-2,2 dimethyl-8-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-octanoic acid, hydrochloride salt

HRID 1801538Notes

Reaction equation

HRID 1801538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:20]1[CH2:25][CH2:24][C:23]2[NH:26][CH:27]=[CH:28][C:22]=2[CH2:21]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH3:19])([CH3:18])[C:15]([OH:17])=[O:16].Cl.O>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:20]1[CH2:25][CH2:24][C:23]2[NH:26][CH:27]=[CH:28][C:22]=2[CH2:21]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH3:19])([CH3:18])[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 569716028-(2-Chlorophenyl)-2,2 dimethyl-8-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-octanoic acid

Product 1

HCID 1317301438-(2-Chlorophenyl)-2,2 dimethyl-8-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-octanoic acid, hydrochloride saltYield 186.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8-(2-Chlorophenyl)-2,2 dimethyl-8-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-octanoic acid (0.09 g, 0.22 mmol) was dissolved in diethyl ether (5 mL) and added to HCl solution (2N HCl in diethyl ether). Water (5 mL) was added and after mixing the organic layer was discarded. The aqueous solution was freeze dried to afford 8-(2-chlorophenyl)-2,2 dimethyl-8-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-octanoic acid, hydrochloride salt (Compound Iq hydrochloride, 0.09 g, 86.5% yield) as a light yellow powder. 1H NMR (Field: 300 MHz, Solvent: CD3OD/TMS) δ (ppm): 10.28 (br, 1H), 7.61 (br s, 1H), 7.48-7.40 (m, 3H), 6.57 (d, 1H, J=10.8 Hz), 5.86-5.70 (2 s, 1H), 4.79-4.52 (m, 3H), 4.19-3.86 (m, 2H), 3.45-2.77 (m, 4H), 2.22-2.06 (m, 2H), 1.26-0.65 (m, 8H), 0.97 (s, 6H). (mixture of conformation isomers in NMR). 13C NMR (Field: 75 MHz, Solvent: CDCl3/TMS) δ (ppm) 181.66, 137.12, 132.64, 132.39, 129.68, 122.62, 119.72, 109.61, 105.95, 105.76, 66.09, 51.79, 50.73, 43.06, 41.57, 37.95, 31.80, 30.52, 26.59, 25.78, 21.67. HRMS (HR, DIP-CI): Calculated for C23H31ClN2O2 (M+H)+: 403.2147, found 403.2158. CHN analysis: Calculated; 62.87 C, 7.34 H, 6.37 N, 16.14 Cl, found; 60.04 C, 7.05 H, 5.92 N, 15.88 Cl.

Workup

  1. additionafter mixing the organic layer
  2. customdried

Sources & evidence

ORD record
ord-ee13850dd153489da66d3537be54937c
Source dataset
uspto-grants-2013_01
Patent number
US08349833B2

Reaction notes

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