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Diisopropylethylamine → N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine

HRID 482279
Notes
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Reaction equation

HRID 482279 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)([OH:16])[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[CH:29]1([CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40]Cl)=[CH:36][CH:35]=2)[CH2:31][CH2:30]1.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CS(C)=O>[CH:29]1([CH2:32][O:33][C:34]2[CH:35]=[CH:36][C:37]([CH2:40][N:13]3[CH2:12][CH2:11][CH:10]([C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:27])[F:28])=[CH:8][CH:7]=4)([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=4)[OH:16])[CH2:15][CH2:14]3)=[CH:38][CH:39]=2)[CH2:30][CH2:31]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 193637461-(Chloromethyl)-4-(cyclopropylmethoxy)benzeneHCID 19363748HCID 19363748, compound

Product 1

HCID 11837562N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidineYield 76.5%

Reagents, catalysts & solvents

1
HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 20.5 grams (0.051 mole) of 4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine, 10.0 grams (0.051 mole) of 4-(cyclopropylmeth-oxy)phenylmethyl chloride (prepared as in Step A of Example 1), and 35.4 mL (0.203 mole) of N,N'-diisopropylethylamine in 200 mL of dimethyl sulfoxide was stirred at ambient temperature for about 18 hours. The reaction mixture was then poured into an aqueous solution saturated with sodium bicarbonate. The mixture was extracted with two portions of ethyl acetate, and the extracts combined. The combination was 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 50% heptane in methylene chloride to 50% acetone in methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 22.0 grams of N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionThe mixture was extracted with two portions of ethyl acetate
  2. dry with materialThe combination was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-826d4af714c84464a2a60771363dccbf
Source dataset
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05795901

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes