Dicyclohexylcarbodiimide → 4-(4-Phenylbutyl)-N-(tetrahydropyran-2-yloxy)benzamide

HRID 365053Notes

Reaction equation

HRID 365053 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1NO.[OH:28][N:29]1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:29][O:28][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][O:20]3)=[O:17])=[CH:18][CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3086974-(4-Phenylbutyl)benzoic acidHCID 13168123Tetrahydropyranyl hydroxylamine

Product 1

HCID 141836904-(4-Phenylbutyl)-N-(tetrahydropyran-2-yloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4-(4-phenylbutyl)benzoic acid (700 mg, 2.8 mmol) in 40 ml of CH2Cl2 under argon was added tetrahydropyranyl hydroxylamine (H2N-OTHP) (654 mg, 2.0 eq.), 1-hydroxybenzotriazole (HOBt) (460 mg, 1.2 eq.), N,N'-dicyclohexylcarbodiimide (700 mg, 1.2 eq.) sequentially. After 0.5 hour at 0° the solution was allowed to warm to room temperature and stir under argon for 4 hours. The solution was filtered, concentrated in vacuo to yield a white solid which was chromatographed on LPS-1 silica gel eluting with 6:4 hexane/EtOAc. Product containing fractions were evaporated to give title compound, an oil 1.0 g (~100%).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. customto yield a white solid which
  4. customwas chromatographed on LPS-1 silica gel eluting with 6:4 hexane/EtOAc
  5. additionProduct containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-fa42442bf3294701a8ef264089fedaf6
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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