Phenol → HCID 20336053, compound

HRID 1706499Notes

Reaction equation

C1(O)C=CC=CC=1.[C:8]1([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCC.[Br:27]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[C:8]1([CH:14]([Br:27])[CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Reactant 5

HCID 996Phenol

HCID 6334Propane

HCID 7187Benzoyl Peroxide

HCID 67184N-bromobutanimide

HCID 12341654(3-Phenoxypropyl)benzene

Product 1

HCID 20336053HCID 20336053, compound

Procedure

Following the above procedure but using phenol in place of m-methoxyphenol, there was prepared 1-phenyl-3-phenoxypropane distilling at 146°-9° C. at 6 torr. This propane derivative was brominated α to the phenyl group with N-bromosuccinimide and benzoyl peroxide to yield 1-phenyl-3-phenoxypropylbromide which compound was in turn reacted with dimethylamine in a sealed reaction vessel to yield N,N-dimethyl 1-phenyl-3-phenoxypropylamine boiling in the range 116°-118° C. at 0.3 torr. The hydrochloride salt was prepared by the above procedure to yield N,N-dimethyl 1-phenyl-3-phenoxy-propylamine hydrochloride melting at 165°-167° C. after recrystallization from an ethyl acetate/acetone solvent mixture.

Sources & evidence

ORD record: ord-1a9b80fce48642a78a70a3cbc0137e42
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04207343

Reaction notes

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