Hydrochloric Acid → 4,4-Difluoroazepane hydrochloride

HRID 1914590Notes

Reaction equation

HRID 1914590 reaction equation
C([Cl:4])(=O)C.C(OC([N:12]1[CH2:18][CH2:17][CH2:16][C:15]([F:20])([F:19])[CH2:14][CH2:13]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[ClH:4].[F:19][C:15]1([F:20])[CH2:16][CH2:17][CH2:18][NH:12][CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 58110242Tert-butyl 4,4-difluoroazepane-1-carboxylate

Product 1

HCID 569243114,4-Difluoroazepane hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Acetyl chloride (3.9 mL) was added to methanol (90 mL) at 0° C. and stirred for 20 minutes before addition of 4,4-difluoro-azepane-1-carboxylic acid tert-butyl ester as a solution in methanol (10 mL). After 30 minutes, HCl in dioxane (4 N, 40 mL) was added cautiously and the mixture was stirred at room temperature for 3 hours. The solution was concentrated, triturated with ether, filtered and dried under vacuum overnight to afford the title compound as an off-white solid (2.1 g). 1H NMR (400 MHz, DMSO): δ 9.5 (s, 2H), 3.2-3.1 (m, 4H), 2.5-2.4 (m, 2H), 2.3-2.2 (m, 2H), 1.9-1.8 (m, 2H).

Workup

  1. concentrationThe solution was concentrated
  2. customtriturated with ether
  3. filtrationfiltered
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-9c32768ee5674f1c92e87cd64a8ca9da
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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