Propanal → HCID 86592015, compound

HRID 1785880Notes

Reaction equation

NC1C=CC(C(N2C3C(=CC=CC=3)[C@H](N(C3C=CC=CC=3)C(=O)CC)C[C@@H]2C)=O)=CC=1.[CH2:32]([CH:34](CC)[CH2:35][NH:36][C:37]1[CH:66]=[CH:65][C:40]([C:41]([N:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C@H:46]([N:53]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:54](=[O:57])[CH2:55][CH3:56])[CH2:45][C@@H:44]2[CH3:64])=[O:42])=[CH:39][CH:38]=1)C.C(=O)CC.C(C(CC)C=O)C>>[CH3:64][C@H:44]1[CH2:45][C@@H:46]([N:53]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:54](=[O:57])[CH2:55][CH3:56])[C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:43]1[C:41](=[O:42])[C:40]1[CH:65]=[CH:66][C:37]([NH:36][CH2:35][CH2:34][CH3:32])=[CH:38][CH:39]=1

Participants

Reactant 4

HCID 527Propanal

HCID 73592-Ethylbutyraldehyde

HCID 86592010HCID 86592010, compound

HCID 86592014HCID 86592014, compound

Product 1

HCID 86592015HCID 86592015, compound

Procedure

(±)-Cis-N-[2-methyl-1-(4-propylamino-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide utilizing the reductive amination conditions described for the synthesis of (±)-cis-N-{1-[4-(2-ethyl-butylamino)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-phenyl-propionamide. Propionaldehyde was substituted for 2-ethylbutyraldehyde. The reaction was poorly selective and afforded approximately equivalent amounts of mono- and di-alkylated products (i.e., (±)-cis-N-[1-(4-dipropylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl propionamidel see below).

Workup

customafforded approximately equivalent amounts of mono- and di-alkylated products (i.e., (±)-cis-N-[1-(4-dipropylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl propionamidel see below)

Sources & evidence

ORD record: ord-290a98cf79694152b7a09c981c128001
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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