Benzyl Chloride → HCID 53635052, compound

HRID 1287850Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:18]([C:22]1[CH:23]=[CH:24][C:25]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[O:29])=[N:26][CH:27]=1)[CH2:19][CH2:20][CH3:21].B(Br)(Br)Br.C(Cl)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:14]([NH2:26])[CH:15]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:18]([C:22]1[CH:23]=[CH:24][C:25]([C:28]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:34]([NH2:7])[CH:35]=2)=[O:29])=[N:26][CH:27]=1)[CH2:19][CH2:20][CH3:21]

Participants

Reactant 4

HCID 7503Benzyl Chloride

HCID 25134Boron tribromide

HCID 21506746(4-Methoxyphenyl)(6-methylpyridin-2-yl)methanone

HCID 54299030HCID 54299030, compound

Product 2

HCID 53635052HCID 53635052, compound

HCID 53657367HCID 53657367, compound

Procedure

4-Methoxyphenyl (6-methyl-2-pyridyl) ketone and 4-methoxyphenyl (5-n-butyl-2-pyridyl) ketone are nitrated, cleaved with BBr3, treated with benzyl chloride and reduced according to the procedures of Example 1 to give 3-amino-4-benzyloxyphenyl (6-methyl-2-pyridyl) ketone and 3-amino-4-benzyloxyphenyl (5-n-butyl-2-pyridyl) ketone. These compounds are substituted for 3-amino-4-benzyloxyphenyl 2-pyridyl ketone in Example 2 to give α-(4-hydroxy-3-ureidophenyl)-6-methyl-2-piperidylcarbinol hydrochloride and α-(4-hydroxy-3-ureidophenyl)-5-n-butyl-2-piperidylcarbinol hydrochloride. The analogous methylureido compounds are prepared as described in Example 2.

Sources & evidence

ORD record: ord-c5509690ac554fc58e9e8938b4831577
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03985887

Reaction notes

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