Toluene → 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-carbonyl]-4-piperidinol

HRID 1449055Notes

Reaction equation

HRID 1449055 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16](Cl)=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:19]([C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([CH3:22])([CH3:21])[CH3:20].C1(C)C=CC=CC=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)C.C(Cl)Cl>[C:19]([C:23]1([OH:29])[CH2:24][CH2:25][N:26]([C:16]([CH:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=3)=[O:17])[CH2:27][CH2:28]1)([CH3:22])([CH3:20])[CH3:21]

Participants

8

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 1251564810,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonyl chlorideHCID 125156594-Tert-butylpiperidin-4-ol

Product 1

HCID 125156604-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-carbonyl]-4-piperidinol

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3 Parts of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carboxylic acid chloride and 1.75 part of 4-tert-butyl-4-piperidinol are admixed in 15 parts by volume of toluene and then 1.5 part of triethylamine is added. The resultant mixture is stirred, at 75° C. under a nitrogen atmosphere for about 1.5 hour and then 5 parts by volume of methylene chloride is added. The mixture is stirred for about 24 hours, and then concentrated on a rotary evaporator to give a tan solid. The solid is redissolved in chloroform, washed with 1 N hydrochloric acid twice, saturated sodium bicarbonate solution, and brine, dried with magnesium sulfate and concentrated in vacuo to give a yellow oil. The oil upon trituration with ethyl ether, affords 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)carbonyl]-4-piperidinol, as a white solid, melting at about 189°-190.5° C. after recrystallization from cyclohexane. This compound is represented by the following structural formula ##STR26##

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customto give a tan solid
  3. washwashed with 1 N hydrochloric acid twice
  4. dry with materialsaturated sodium bicarbonate solution, and brine, dried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-87ca09359f184d8a9a277b2a04ecd5e0
Source dataset
uspto-grants-1980_02
Patent number
US04188485

Reaction notes

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