Thionyl Chloride → HCID 22122083, compound

HRID 1858939Notes

Reaction equation

HRID 1858939 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[C:10]1([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH:23]3[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O=S(Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:26]2[CH2:27][CH2:28][CH:23]([N:20]3[CH2:21][CH2:22][CH:17]([CH2:16][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH2:18][CH2:19]3)[CH2:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 15338142HCID 15338142, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 22122083HCID 22122083, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorophenyl magnesium bromide (10 mmole) and 4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanone (7.38 mmole) were reacted by the method described in Example 13 to give the intermediate mixture of cis and trans alcohols. This crude mixture was then dehydrated using SOCl2 in CH2Cl2 by the method described in Example 35 to give the crude product which was purified by chromatography on silica gel using ethyl acetate as the eluent. The pure product was converted the HCl salt in acetone using 12N HCl (23.3% overall, mp: 214-217° C.). Calc'd for C24H28NF.HCl.0.25H2O: C, 73.83%; H, 7.62%; N, 3.59%. Found: C, 73.85%; H, 7.61%; N, 3.56%.

Workup

  1. customto give

Sources & evidence

ORD record
ord-522b264e3f2949d095464421e7ec3d99
Source dataset
uspto-grants-2000_11
Patent number
US06153611

Reaction notes

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