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

HRID 1526466Notes

Reaction equation

HRID 1526466 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:19]1[CH2:24][CH2:23][C:22]2[NH:25][CH:26]=[CH:27][C:21]=2[CH2:20]1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15].Cl>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:19]1[CH2:24][CH2:23][C:22]2[NH:25][CH:26]=[CH:27][C:21]=2[CH2:20]1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 569713847-(2-Chlorophenyl)-2,2 dimethyl-7-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-heptanoic acid

Product 1

HCID 1317301447-(2-Chlorophenyl)-2,2 dimethyl-7-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-heptanoic acid, hydrochlorideYield 133.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7-(2-Chlorophenyl)-2,2 dimethyl-7-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-heptanoic acid (0.26 g, 0.67 mmol) was dissolved in diethyl ether (15 mL) and hydrogen chloride solution (2N HCl in diethyl ether) was added. The ether solution was extracted with water (15 mL) and the organic layer was discarded. The aqueous solution was freeze dried to afford 7-(2-chlorophenyl)-2,2 dimethyl-7-(1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-yl)-heptanoic acid, hydrochloride (Compound Ik hydrochloride, 0.19 g, 61.9% yield) as a light yellow powder (purity 97.33% by HPLC, mp. 168-172° C.). 1H NMR (Field: 300 MHz, Solvent: CD3OD/TMS) δ (ppm): 10.26 (br s, 1H), 7.65 (br s, 1H), 7.45-7.38 (m, 4H), 6.54-6.50 (2 s, 1H), 5.84 (s, 0.5H), 5.66 (s, 0.5H), 4.79 (m, 1H), 4.51 (m, 1H), 4.14-3.82 (m, 2H), 3.43-2.76 (m, 4H), 2.43-2.09 (m, 2H), 1.25-1.14 (m, 4H), 1.39-0.65 (m, 2H), 0.96 (s, 6H). (mixture of conformational isomers). 13C NMR (Field: 75 MHz, Solvent: CDCl3/TMS) 6 (ppm) 181.52, 137.17, 132.64, 132.32, 131.75, 130.09, 129.79, 122.85, 119.88, 109.70, 106.00, 65.79, 51.79, 51.10, 42.98, 41.43, 31.84, 27.28, 25.096, 25.76, 21.78. MS (HR, DIP-CI): Calculated for C22H30Cl2N2O2 (M+H)+: 389.1994. found 389.1996. CHN analysis: Calculated; 62.12; C, 7.11; H, 6.59; N, 16.67; Cl. Found; 59.23; C, 7.04; H, 6.26; N, 16.93; Cl.

Workup

  1. extractionThe ether solution was extracted with water (15 mL)
  2. customdried

Sources & evidence

ORD record
ord-ef9a3ab631fb4e15ac1e11c5ea5dd217
Source dataset
uspto-grants-2015_07
Patent number
US09085585B2

Reaction notes

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