Reaction equation
OCC1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[NH:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@H:7]1[NH:15][CH3:16].Br[CH2:22][CH2:23]Br.C(N(CC)CC)C.[Br-].C([NH+](CC)CC)C.C([O:42][CH2:43][CH3:44])C>>[OH:42][CH2:43][C:44]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[N:5]1[CH2:23][CH2:22][N:15]([CH3:16])[C@@H:7]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C@@H:6]12Participants
Reactant 5
Product 1
Procedure
A solution of trans 1-(2-hydroxymethylanilino)-2-methylaminoindane (1.16 kg; 4.3 moles) in 1,2-dibromoethane (7 l, 17.1 moles) and triethylamine (2.5 l; 34 moles) was added dropwise to stirred 1,2-dibromoethane (13 l; 31.9 moles) at ca. 100° over a period of 1.5 h. This was followed by triethylamine (2.5 l; 34 moles) added dropwise over 30 min. The reaction was cooled to 50° and diethyl ether (80 l) was added with good stirring. After stirring for 1 h the precipitated triethylammonium bromide was filtered off and the resulting solution concentrated in vacuo to ca 3.5 l. Addition of ethyl acetate (2.5 l) assisted crystallisation of the required product. Filtration and trituration (pet. ether) afforded the title compound as a white crystalline solid (687 g; 54%) m.p. 166-7°.
Workup
- additionadded dropwise over 30 min
- temperatureThe reaction was cooled to 50°
- filtrationwas filtered off
- concentrationthe resulting solution concentrated in vacuo to ca 3.5 l
- additionAddition of ethyl acetate (2.5 l)
- customcrystallisation of the required product
- filtrationFiltration and trituration (pet. ether)
Sources & evidence
- ORD record
- ord-99229bb631914e70bcc59958c9111900
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04585588
Linked notes
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