Chloroacetyl chloride → (10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-[2-(spiro[isochroman-1,4'-piperidin]-1'-yl)-ethyl]-amine hydrochloride

HRID 1276631Notes

Reaction equation

[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[Cl:17][CH2:18][C:19](Cl)=O.[NH:22]1[CH2:27][CH2:26][C:25]2([C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][CH2:29][O:28]2)[CH2:24][CH2:23]1>>[ClH:17].[CH:12]1[C:7]2[CH2:6][CH2:5][C:4]3[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=3[CH:2]([NH:1][CH2:18][CH2:19][N:22]3[CH2:27][CH2:26][C:25]4([C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30][CH2:29][O:28]4)[CH2:24][CH2:23]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 81481Iem 2115

HCID 151870503,4-Dihydrospiro[2-benzopyran-1,4'-piperidine]

Product 1

HCID 22116575(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-[2-(spiro[isochroman-1,4'-piperidin]-1'-yl)-ethyl]-amine hydrochloride

Procedure

The title compound, m.p. 190° C. and MS: m/e=439.4 (M+H+), was prepared in accordance with the general method of example 1 from 5-amino-10,11-dihydro-5H-dibenzo[a,d]cycloheptene, chloroacetyl chloride, spiro[isochroman-1,4'-piperidine] and Hcl.

Sources & evidence

ORD record: ord-3cbb5ea8b3c646d6a01bcfe689ba0079
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166209

Reaction notes

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