Dichloromethane → Hydrochloric Acid

HRID 511081Notes

Reaction equation

HRID 511081 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:25][N:24]([CH3:26])[NH:23][N:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl:34]CCl>>[ClH:34].[CH3:26][N:24]1[NH:23][N:22]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:16][CH:17]=2)[NH:25]1.[ClH:34]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66693371HCID 66693371, compound

Product 2

HCID 313Hydrochloric AcidHCID 66680606HCID 66680606, compound

Procedure

4-[4-(1-Methyl-1H-tetrazol-5-yl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (401 mg; 1.12 mmol, prepared in accordance with Example 19) is dissolved in dichloromethane (3 mL) and trifluoroacetic acid (1 mL) is slowly added under stirring. After 60 minutes reaction time, the mixture is concentrated under reduced pressure and co-evaporated twice with dichloromethane (10 mL). The crude residue is then diluted in dioxane (2 mL) and a 4N solution of hydrochloric acid in dioxane (3 mL) is added under stiffing. The solid formed is filtered and is dried under high vacuum to afford the desired product as hydrochloride (257 mg; 0.87 mmol).

Workup

  1. customAfter 60 minutes reaction time
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionThe crude residue is then diluted in dioxane (2 mL)
  4. additiona 4N solution of hydrochloric acid in dioxane (3 mL) is added under stiffing
  5. customThe solid formed
  6. filtrationis filtered
  7. customis dried under high vacuum

Sources & evidence

ORD record
ord-8f2533227a9c43bb9473cb8369f883c2
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

Loading…