(Diethylamino)sulfur trifluoride → HCID 19040919, compound

HRID 866068Notes

Reaction equation

HRID 866068 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]([C:31]3[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=3)([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)O)[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].C(N(S(F)(F)[F:48])CC)C>C(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]([C:31]3[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=3)([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[F:48])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 15515183HCID 15515183, compound

Product 1

HCID 19040919HCID 19040919, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 0.6 gram (0.001 mole) of N-(4-propoxyphenylmethyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine (prepared in Example 10) in 15 mL of methylene chloride was cooled to -78° C., and 0.15 mL (0.001 mole) of diethylaminosulphur trifluoride (DAST) was added via a syringe. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature as it stirred for about 18 hours. After this time, the reaction mixture was poured into ice-water. The mixture was then extracted with two 50 mL portions of methylene chloride. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of 5-15% acetone in methylene chloride as the eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about 0.1 gram of N-(4-propoxyphenylmethyl)-4-[bis(4-trifluoromethoxyphenyl)fluoromethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionThe mixture was then extracted with two 50 mL portions of methylene chloride
  3. dry with materialThe combined extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d32c08284a848b584a776a4953a5e2d
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

Loading…