Benzhydrol → HCID 2344, compound
Reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][N:16]1[CH:20]2[CH2:21][CH:22](O)[CH2:23][CH:17]1[CH2:18][CH2:19]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:14][CH:22]2[CH2:21][CH:20]3[N:16]([CH3:15])[CH:17]([CH2:18][CH2:19]3)[CH2:23]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
The starting material is prepared as follows. The intimate mixture of 9.20 g of benzhydrol 7.05 g of tropine and 10 g of p-toluenesulfonic acid monohydrate is placed in a flask which is fitted with an air condensor and a vacuum take-off. The flask is evacuated and maintained in vacuo while being heated in an oil bath to 165°-170°, whereby the liberated water is removed. After 2 hours, the mixture is cooled and partitioned between 100 ml of water and diethyl ether each. The aqueous solution is separated, washed once more with diethyl ether and made basic with 50% aqueous sodium hydroxide. It is extracted repeatedly with diethyl ether, the extract washed with brine and evaporated to give 3-diphenylmethoxy-8-methyl-8-azabicyclo[3.2.1]octane, which is sufficiently pure to be used in the next step.
Workup
- customThe starting material is prepared
- customis placed in a flask
- customwhich is fitted with an air condensor
- customThe flask is evacuated
- temperaturemaintained in vacuo
- temperaturewhile being heated in an oil bath to 165°-170°
- customwhereby the liberated water is removed
- temperaturethe mixture is cooled
- custompartitioned between 100 ml of water and diethyl ether each
- customThe aqueous solution is separated
- washwashed once more with diethyl ether
- extractionIt is extracted repeatedly with diethyl ether
- washthe extract washed with brine
- customevaporated
Sources & evidence
- ORD record
- ord-e366432265fb4da2a2e973a42e53e5b8
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04261990
Reaction notes
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