p-Fluorophenethylamine → HCID 57166725, compound

HRID 1653689Notes

Reaction equation

HRID 1653689 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[CH:13]1([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CCCCCC.C(OC(=O)C)C.[F:33][C:34]1[CH:39]=[CH:38][C:37](CCN)=[CH:36][CH:35]=1>C(Cl)Cl>[CH:13]1([CH2:19][O:20][C:1]([NH:8][CH2:12][CH2:11][C:37]2[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=2)=[O:2])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 4653p-Fluorophenethylamine2×HCID 7507Cyclohexanemethanol2×HCID 682631,1'-CarbonyldiimidazoleHCID 21226206Ethyl acetate hexane

Product 1

HCID 57166725HCID 57166725, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.87 g (30 mmol) of carbonyldiimidazole and 3.43 g (30 mmol) of cyclohexylmethanol was stirred, under nitrogen and at room temperature, for 2-4 hours or the time until the TLC (silica gel; hexane-ethylacetate, 4:1) analysis indicated a complete disappearance of cyclohexylmethanol in the mixture. To this reaction mixture, a solution of 4-fluorophenylethyl amine (4.18 g, 30 mmol) in methylene chloride (5 mL) was added and stirred overnight. The TLC analysis indicated a complete disappearence of 4-fluorophenylethyl amine. The reaction mixture was extracted with 4×50 mL of methylene chloride. The combined extracts were washed with 5% HCl (2×50 mL), water, dried over MgSO4, and concentracted under vacuum. The solid was crystallized from hexane to furnish 5.0 g of N-(Cyclohexylmethyloxycarbonyl)-4-fluorophenylethyl amine (59% yield). mp 44°-45° C.

Workup

  1. extractionThe reaction mixture was extracted with 4×50 mL of methylene chloride
  2. washThe combined extracts were washed with 5% HCl (2×50 mL), water
  3. dry with materialdried over MgSO4
  4. customThe solid was crystallized from hexane

Sources & evidence

ORD record
ord-33629e6b5f324572a83243cdcb2bb4cf
Source dataset
uspto-grants-1995_04
Patent number
US05403851

Reaction notes

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