Pyrrolidine → Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl](2-pyrrolidin-1-ylethyl)amine

HRID 2423640Notes

Reaction equation

HRID 2423640 reaction equation
ClCC(N(CC)C1C=C(OC)C=CC=1C1CCC2C(=CC=C(OC)C=2)C1)=O.N1CCCC1.[CH2:33]([N:35]([C:44]1[CH:49]=[C:48]([O:50][CH3:51])[CH:47]=[CH:46][C:45]=1[CH:52]1[CH2:61][CH2:60][C:59]2[C:54](=[CH:55][CH:56]=[C:57]([O:62][CH3:63])[CH:58]=2)[CH2:53]1)[C:36](=O)[CH2:37][N:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1)[CH3:34]>>[CH2:33]([N:35]([C:44]1[CH:49]=[C:48]([O:50][CH3:51])[CH:47]=[CH:46][C:45]=1[CH:52]1[CH2:61][CH2:60][C:59]2[C:54](=[CH:55][CH:56]=[C:57]([O:62][CH3:63])[CH:58]=2)[CH2:53]1)[CH2:36][CH2:37][N:38]1[CH2:39][CH2:40][CH2:41][CH2:42]1)[CH3:34]

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 579341032-chloro-N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamideHCID 66626207N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2-pyrrolidin-1-ylacetamide

Product 1

HCID 66626973Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl](2-pyrrolidin-1-ylethyl)amineYield 83.4%

Procedure

Synthesized from 2-chloro-N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide and pyrrolidine according to an analogous synthetic method to Preparation Example 89, N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2-pyrrolidin-1-ylacetamide (119 mg) was used according to an analogous synthetic method to Example 337 described below to provide ethyl [5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl](2-pyrrolidin-1-ylethyl)amine (96 mg). This compound (95 mg) was used according to an analogous synthetic method to Example 111 described below to provide the title compound (92 mg).

Sources & evidence

ORD record
ord-500bcb943b6e4b148fcd939ea95b624c
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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