1-Bromopropane → 1-(3-Chlorophenoxy)-3-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2107697Notes

Reaction equation

C(O)(=O)C(O)=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][NH:14][CH2:13]1.Br[CH2:27][CH2:28][CH3:29].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][N:14]([CH2:27][CH2:28][CH3:29])[CH2:13]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-(m-chlorophenoxy)-2,3,4,5-tetrahydro-3-benzazepine of Example 4 (6.4 g, 0.023 mole), 1-bromopropane (5.7 g., 0.047 mole) and sodium bicarbonate (8.4 g, 0.10 mole) in DMF (100 ml) was stirred at 70° C. for three hours. The mixture was concentrated under high vacuum to an oil which was stirred with water then extracted with ether. The ether extracts were washed twice with water and dried (saturated NaCl, anhydrous MgSO4). The solution was filtered, then concentrated to an oil (6.3 g, 86%) which was distilled to yield an oil of 1-(m-chlorophenoxy)-3-(n-propyl)-2,3,4,5-tetrahydro-3-benzazepine, 190°-210° C./0.1 mm.

Workup

concentrationThe mixture was concentrated under high vacuum to an oil which
stirringwas stirred with water
extractionthen extracted with ether
washThe ether extracts were washed twice with water
dry with materialdried (saturated NaCl, anhydrous MgSO4)
filtrationThe solution was filtered
concentrationconcentrated to an oil (6.3 g, 86%) which
distillationwas distilled

Sources & evidence

ORD record: ord-25f156b582004742bd8a13dafc49e395
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935418

Reaction notes

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