Diisopropylethylamine → HCID 11837562, compound

HRID 1683849Notes

Reaction equation

HRID 1683849 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12]Cl)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[F:14][C:15]([F:41])([F:40])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)([OH:29])[CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.C(Cl)Cl.CC(C)=O.CCCCCCC>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:26]3[CH2:27][CH2:28][CH:23]([C:22]([C:30]4[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:34][CH:35]=4)([C:19]4[CH:20]=[CH:21][C:16]([C:15]([F:14])([F:40])[F:41])=[CH:17][CH:18]=4)[OH:29])[CH2:24][CH2:25]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 3

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

Product 1

HCID 11837562HCID 11837562, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent4×HCID 8900HeptaneSolvent2×

Procedure

This compound was prepared in a manner analogous to that of Step D of Example 12, with 0.4 gram (0.002 mole) of 4-(cyclopropylmethoxy)phenylmethyl chloride (prepared as in Step A of Example 16), 0.9 gram (0.002 mole) of 4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine, and 1.1 grams (0.008 mole) of N, N-diisopropylethylamine in about 30 mL of dimethyl sulfoxide as reagents. The crude reaction product was subjected to column chromatography on silica gel with 1:1 heptane:methylene chloride, pure methylene chloride, 11:10 heptane:methylene chloride, and 1:10 acetone:methylene chloride used succesively as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.8 gram of N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 12
  2. customThe crude reaction product
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7a2e78ff6a54debafd64c0d16028585
Source dataset
uspto-grants-1997_06
Patent number
US05639763

Reaction notes

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