Diisopropylethylamine → HCID 86717901, compound

HRID 2275825Notes

Reaction equation

HRID 2275825 reaction equation
Cl.[F:2][C:3]1([F:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Br[CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(N(CC)C(C)C)(C)C>C(#N)C>[F:2][C:3]1([F:9])[CH2:8][CH2:7][N:6]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate2×

Product 1

HCID 86717901HCID 86717901, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

0.90 g of 4,4-difluoropiperidine hydrochloride (5.71 mmol, 1 equivalents) were initially charged in 56 ml of acetonitrile, 1.41 g of tert-butyl (2-bromoethyl)carbamate (6.28 mmol, 1.1 equivalents) and 3 ml of N,N-diisopropylethylamine (2.21 g, 17.13 mmol, 3 equivalents) were added and the mixture was stirred at 80° C. overnight. Twice, 0.4 equivalent of tert-butyl (2-bromoethyl)carbamate was added to the reaction solution, and in each case stirring was continued at 80° C. overnight. The mixture was concentrated and purified on a silica gel column (gradient: from cyclohexane/ethyl acetate: 3:1 to ethyl acetate). This gave 1.28 g (62% of theory; purity 73%) of the title compound.

Workup

  1. stirringin each case stirring
  2. waitwas continued at 80° C. overnight
  3. concentrationThe mixture was concentrated
  4. custompurified on a silica gel column (gradient: from cyclohexane/ethyl acetate: 3:1 to ethyl acetate)

Sources & evidence

ORD record
ord-08d9f07414e04ed4aeb885701bc88b74
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…