Hydrochloric Acid → 6-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid hydrochloride salt

HRID 873403Notes

Reaction equation

HRID 873403 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:19]([O:21]C)=[O:20])[C:5]2[C:6]([CH3:18])=[C:7]([CH2:14][N:15]([CH3:17])[CH3:16])[N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.Cl>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:19]([OH:21])=[O:20])[C:5]2[C:6]([CH3:18])=[C:7]([CH2:14][N:15]([CH3:16])[CH3:17])[N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67468936methyl 6-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylate

Product 1

HCID 674684516-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid hydrochloride saltYield 178.4%

Conditions

Temperature
80 °C

Procedure

To methyl 6-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylate (0.44 g, 1.363 mmol) was added 6 N HCl (20 ml, 120 mmol). The reaction was purged with N2, attached a reflux condensor, heated to 80° C., and stirred for 18 hr. LCMS showed that the reaction was complete. The reaction was cooled to RT, diluted with an equal volume of water, washed with EtOAc, and evaporated to dryness under vacuum to give the product 6-chloro-2-((dimethylamino)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid hydrochloride salt (0.42 g, 1.216 mmol, 89% yield) as a beige solid. (86% pure by LCMS, contains ˜10% of the des-chloro side product from the previous reaction.) Used as is in the next step. 1H NMR (400 MHz, DMSO-d6) δ=13.19 (br. s., 1 H), 10.45 (br. s., 1 H), 7.90 (d, J=1.8 Hz, 1 H), 7.33 (d, J=1.8 Hz, 1 H), 4.91 (quin, J=6.9 Hz, 1 H), 4.58 (d, J=5.6 Hz, 2 H), 2.79 (d, J=4.8 Hz, 6 H), 2.34 (s, 3 H), 1.58 (d, J=6.8 Hz, 6 H). MS(ES)+m/e 309.2 [M+H]+, 264.1 [M+H]+ −45 (HNMe2).

Workup

  1. customThe reaction was purged with N2
  2. temperatureThe reaction was cooled to RT
  3. additiondiluted with an equal volume of water
  4. washwashed with EtOAc
  5. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-c52b4736df4b47d397dde0c1312e3951
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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