Hydrochloric Acid → HCID 70553065, compound

HRID 1156701Notes

Reaction equation

C1(C)C=CC=C([Cl:7])C=1.Cl.[C:10]([NH:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=2)=[C:20]([O:32][C:33]2[CH:34]=[C:35]([CH3:39])[CH:36]=[CH:37][CH:38]=2)[CH:19]=1)=[O:17])([CH3:13])([CH3:12])[CH3:11].Cl>>[ClH:7].[C:35]1([CH3:39])[CH:36]=[CH:37][CH:38]=[C:33]([O:32][C:20]2[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=2[O:24][C:25]2[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=2)[CH:16]([OH:17])[CH2:15][NH:14][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:34]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 79313-Chlorotoluene

HCID 70554858HCID 70554858, compound

Product 1

HCID 70553065HCID 70553065, compound

Procedure

Following a procedure similar to that described above in Example 111 but using m-toluyl chloride instead of o-toluyl chloride, there was obtained 14 g. of 3,4-bis(m-toluyloxy)phenyl tert-butylaminomethyl ketone hydrochloride as a white crystalline solid which melted at 215°-218° C. When 19 g. of this hydrochloride (5 g. of which was obtained from a second run) was catalytically hydrogenated, using a procedure similar to that described above in Example 30B, there was obtained 3,4-bis(m-toluyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride which was converted to the free base and then to the methanesulfonate, a white crystalline solid which weighed 12.0 g. and melted at 135° C. (uncorr.).

Workup

customthere was obtained 14 g
customof which was obtained from a second run)

Sources & evidence

ORD record: ord-e601192d94394fbd8f72de4e8adee509
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04336400

Reaction notes

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