Water → HCID 57892436, compound

HRID 1821096Notes

Reaction equation

HRID 1821096 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:16]([N:17]=[C:18]3[C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:15][C:14]([Cl:24])=[CH:13][CH:12]=2.[CH2:25]([O:32][C:33]1[CH:42]=[CH:41][C:40]2[C@@H:39]([NH2:43])[CH2:38][CH2:37][CH2:36][C:35]=2[N:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C)C=O>[CH2:25]([O:32][C:33]1[CH:42]=[CH:41][C:40]2[C@H:39]([NH:43][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]3[C:11]4[C:16]([N:17]=[C:18]5[C:23]=3[CH2:22][CH2:21][CH2:20][CH2:19]5)=[CH:15][C:14]([Cl:24])=[CH:13][CH:12]=4)[CH2:38][CH2:37][CH2:36][C:35]=2[N:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9943023(S)-2-benzyloxy-5,6,7,8-tetrahydro-quinolin-5-ylamineHCID 11223585HCID 11223585, compound

Product 1

HCID 57892436HCID 57892436, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (7-bromo-heptyl)-(6-chloro-1,2,3,4-tetrahydro-acridin-9-yl)-amine (180 mg, 0.43 mmoL) and (S)-2-benzyloxy-5,6,7,8-tetrahydro-quinolin-5-ylamine (108 mg, 0.43 mmoL) in dried N,N-dimethylformamide (2.1 ml) was heated up to 120 degree Celsius under nitrogen for 5 h. After cooling to room temperature, the reaction mixture was poured into icy water. The mixture was extracted with ethyl acetate. The combined ethyl acetate was dried, filtered and concentrated. The resulting crude product was purified by column chromatography on silica gel using hexane/ethyl acetate/triethyl amine (8/2/1) to give the desired product (80 mg, 0.14 mmoL) in 33% yield.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe combined ethyl acetate was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2f5a716b1f4043868d8653f82d4b53df
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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